Oxathiin carboxamide

ABSTRACT

This invention relates to novel oxathiincarboxamides of the formula (I)  
                 
         in which G 1 , G 2 , G 3 , n, R 1 , R 2 , R 3 , R 4 , R 5  and Z are as defined in the disclosure, to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and to novel intermediates and their preparation.

The present invention relates to novel oxathiincarboxamides, to aplurality of processes for their preparation and to their use forcontrolling unwanted microorganisms.

It is already known that numerous carboxamides have fungicidalproperties (cf., for example, EP-A 0 591 699, EP-A 0 545 099, DE-A 16 17921, JP-A 2001-302605, JP-A 10-251240, JP-A 8-176112, JP-A 53-72823 andU.S. Pat. No. 3,657,449).

Thus, a number of 6-methyl-2,3-dihydro-1,4-oxathiin-5-carboxamides havealready been disclosed.N-(4′-Fluoro-1,1′-biphenyl-2-yl)-6-methyl-2,3-dihydro-1,4-oxathiin-5-carboxamideand(6-methyl-(2,3-dihydro-1,4-oxathiin-5-yl))-N-[2-(2-methylpropyl)phenyl]carboxamidefrom EP-A 0 545 099,(6-methyl-(2,3-dihydro-1,4-oxathiin-5-yl))-N-(2,4,6-trimethyl-phenyl)carboxamidefrom DE-A 16 17 921,N-[2-(1,3-dimethylbutyl)phenyl](6-methyl-(2,3-dihydro-1,4-oxathiin-5-yl))carboxamidefrom JP-A 10-251240 and(6-methyl-(2,3-dihydro-1,4-oxathiin-5-yl))-N-(2-methylphenyl)carboxamidefrom U.S. Pat. No. 3,657,449 may be mentioned by way of example. Theactivity of these compounds is good; however, in some cases, for exampleat low application rates, it is unsatisfactory.

This invention now provides novel oxathiincarboxamides of the formula(I)

in which

-   G¹ represents halogen, trifluoromethyl, difluoromethyl or    cyclopropyl,-   G² and G³ independently of one another represent hydrogen or methyl,-   n represents 0, 1 or 2,-   R¹, R², R³ and R⁴ independently of one another represent hydrogen,    fluorine, chlorine, methyl, isopropyl or methylthio,-   R⁵ represents hydrogen, C₁-C₈-alkyl, C₁-C₆-alkylsulfinyl,    C₁-C₆-alkylsulfonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl;    C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl,    C₁-C₄-haloalkylsulfonyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms, formyl-C₁-C₃-alkyl,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;    (C₁-C₃-haloalkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 7    fluorine, chlorine and/or bromine atoms,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-haloalkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 6    fluorine, chlorine and/or bromine atoms,    (C₁-C₃-haloalkyl)carbonyl-C₁-C₃-haloalkyl,    (C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to    13 fluorine, chlorine and/or bromine atoms; —COR⁶, —CONR⁷R⁸ or    —CH₂NR⁹R¹⁰,-   R⁶ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,    C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl; C₁-C₆-haloalkyl,    C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms; —COR¹¹,-   R⁷ and R⁸ independently of one another represent hydrogen,    C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl;    C₁-C₈-haloalkyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl    having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,-   R⁷ and R⁸ furthermore together with the nitrogen atom to which they    are attached form a saturated heterocycle having 5 to 8 ring atoms,    where the heterocycle may contain 1 or 2 further nonadjacent    heteroatoms from the group consisting of oxygen, sulfur and NR¹² and    is optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen and C₁-C₄-alkyl,-   R⁹ and R¹⁰ independently of one another represent hydrogen,    C₁-C₈-alkyl, C₃-C₈-cycloalkyl; C₁-C₈-haloalkyl, C₃-C₈-halocycloalkyl    having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,-   R⁹ and R¹⁰ furthermore together with the nitrogen atom to which they    are attached form a saturated heterocycle having 5 to 8 ring atoms,    where the heterocycle may contain 1 or 2 further nonadjacent    heteroatoms from the group consisting of oxygen, sulfur and NR¹² and    is optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen and C₁-C₄-alkyl,-   R¹¹ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,    C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl; C₁-C₆-haloalkyl,    C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms,-   R¹² represents hydrogen or C₁-C₆-alkyl,-   Z represents Z¹, Z², Z³ or Z⁴, where

Z¹ represents phenyl which is optionally mono- to pentasubstituted byidentical or different substituents,

-   Z² represents cycloalkyl or bicycloalkyl which is optionally mono-    or polysubstituted by identical or different substituents,-   Z³ represents unsubstituted C₂-C₂₀-alkyl or represents C₁-C₂₀-alkyl    which is mono- or polysubstituted by identical or different    substituents from the group consisting of halogen and    C₃-C₆-cycloalkyl, where the cycloalkyl moiety for its part may    optionally be mono- or polysubstituted by identical or different    substituents from the group consisting of halogen and C₁-C₄-alkyl,-   Z⁴ represents C₂-C₂₀-alkenyl or C₂-C₂₀-alkynyl which is in each case    optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen and    C₃-C₆-cycloalkyl, where the cycloalkyl moiety for its part may    optionally be mono- or polysubstituted by identical or different    substituents from the group consisting of halogen and C₁-C₄-alkyl,-    or-   R¹, R² and R³ independently of one another represent hydrogen or    fluorine and-   Z and R⁴ together with the carbon atoms to which they are attached    form an optionally substituted 5- or 6-membered carbocyclic or    heterocyclic ring.

Furthermore, it has been found that oxathiincarboxamides of the formula(I) are obtained whena) oxathiincarboxylic acid derivatives of the formula (II)

-   -   in which    -   G¹, G², G³ and n are as defined above,    -   X¹ represents halogen or hydroxyl,    -   are reacted with aniline derivatives of the formula (III)    -   in which    -   R¹, R², R³, R⁴, R⁵ and Z are as defined above,    -   if appropriate in the presence of a catalyst, if appropriate in        the presence of a condensing agent, if appropriate in the        presence of an acid binder and if appropriate in the presence of        a diluent, or        b) halooxathiincarboxamides of the formula (IV)    -   in which    -   G¹, G², G³, n, R¹, R², R³, R⁴ and R⁵ are as defined above,    -   X² represents bromine or iodine,    -   are reacted with boronic acid derivatives of the formula (V)    -   in which    -   Z¹ is as defined above and    -   A¹ and A² each represent hydrogen or together represent        tetramethylethylene,    -   in the presence of a catalyst, if appropriate in the presence of        an acid binder and if appropriate in the presence of a diluent,        or        c) oxathiincarboxamide boronic acid derivatives of the formula        (VI)    -   in which    -   G¹, G², G³, n, R¹, R², R³, R⁴ and R⁵ are as defined above,    -   A³ and A⁴ each represent hydrogen or together represent        tetramethylethylene,    -   are reacted with phenyl derivatives of the formula (VII)        X³-Z¹  (VII)    -   in which    -   Z¹ is as defined above and    -   X³ represents chlorine, bromine, iodine or        trifluoromethylsulfonate,    -   in the presence of a catalyst, if appropriate in the presence of        an acid binder and if appropriate in the presence of a diluent,        or        d) halooxathiincarboxamides of the formula (IV)    -   in which    -   G¹, G², G³, n, R¹, R², R³, R⁴ and R⁵ are as defined above,    -   X² represents bromine or iodine,    -   are reacted with phenyl derivatives of the formula (VII)        X³-Z¹  (VII)    -   in which    -   Z¹ is as defined above and    -   X³ represents chlorine, bromine, iodine or        trifluoromethylsulfonate,    -   in the presence of a palladium or nickel catalyst and in the        presence of        4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, if        appropriate in the presence of an acid binder and if appropriate        in the presence of a diluent, or        e) oxathiincarboxamides of the formula (Ia)    -   in which    -   G¹, G², G³, n, R¹, R², R³, R⁴ and R⁵ are as defined above,    -   X⁴ represents C₂-C₂₀-alkenyl or C₂-C₂₀-alkynyl, each of which is        optionally mono- or polysubstituted by identical or different        substituents from the group consisting of halogen and        C₃-C₆-cycloalkyl, where the cycloalkyl moiety for its part may        optionally be substituted by halogen and/or C₁-C₄-alkyl,    -   are hydrogenated, if appropriate in the presence of a diluent        and if appropriate in the presence of a catalyst, or        f) hydroxyalkyloxathiincarboxamides of the formula (VIII)    -   in which    -   G¹, G², G³, n, R¹, R², R³, R⁴ and R⁵ are as defined above,    -   X⁵ represents C₂-C₂₀-hydroxyalkyl which is optionally        additionally mono- or polysubstituted by identical or different        substituents from the group consisting of halogen and        C₃-C₆-cycloalkyl, where the cycloalkyl moiety for its part may        optionally be substituted by halogen and/or C₁-C₄-alkyl,    -   are dehydrated, if appropriate in the presence of a diluent and        if appropriate in the presence of an acid, or        g) halooxathiincarboxamides of the formula (IV)    -   in which    -   G¹, G², G³, n, R¹, R², R³, R⁴ and R⁵ are as defined above,    -   X² represents bromine or iodine,    -   are reacted with an alkyne of the formula (IX)        HC        A⁵  (IX),    -   in which    -   A⁵ represents C₂-C₁₈-alkyl, each of which is optionally mono- or        polysubstituted by identical or different substituents from the        group consisting of halogen and C₃-C₆-cycloalkyl, where the        cycloalkyl moiety for its part may optionally be substituted by        halogen and/or C₁-C₄-alkyl,    -   or an alkene of the formula (X)    -   in which    -   A⁶, A⁷ and A⁸ independently of one another each represent        hydrogen or alkyl which is optionally mono- or polysubstituted        by identical or different substituents from the group consisting        of halogen and C₃-C₆-cycloalkyl, where the cycloalkyl moiety for        its part may optionally be substituted by halogen and/or        C₁-C₄-alkyl and the total number of carbon atoms of the        open-chain part of the molecule does not exceed the number 20,    -   if appropriate in the presence of a diluent, if appropriate in        the presence of an acid binder and in the presence of one or        more catalysts, or        h) ketones of the formula (XI)    -   in which    -   G¹, G², G³, n, R¹, R², R³, R⁴ and R⁵ are as defined above,    -   A⁹ represents hydrogen or C₁-C₁₈-alkyl which is optionally mono-        or polysubstituted by identical or different substituents from        the group consisting of halogen and C₃-C₆-cycloalkyl, where the        cycloalkyl moiety for its part may optionally be substituted by        halogen and/or C₁-C₄-alkyl,    -   are reacted with a phosphorus compound of the formula (XII)        A¹⁰-Px  (XII),    -   in which    -   A¹⁰ represents C₁-C₁₈-alkyl which is optionally mono- or        polysubstituted by identical or different substituents from the        group consisting of halogen and C₃-C₆-cycloalkyl, where the        cycloalkyl moiety for its part may optionally be substituted by        halogen and/or C₁-C₄-alkyl,    -   Px represents a grouping —P⁺(C₆H₅)₃Cl⁻, —P⁺(C₆H₅)₃Br⁻,        —P⁺(C₆H₅)₃I⁻, —P(═O)(OCH₃)₃ or —P(═O)(OC₂H₅)₃,    -   if appropriate in the presence of a diluent, or        i) oxathiincarboxamides of the formula (Ib)    -   in which    -   G¹, G², G³, n, R¹, R², R³, R⁴ and Z are as defined above,    -   are reacted with halides of the formula (XIII)        R⁵⁻¹—X⁶  (XIII)    -   in which    -   R⁵⁻¹ represents C₁-C₈-alkyl, C₁-C₆-alkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl;        C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl,        C₁-C₄-haloalkylsulfonyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine,        chlorine and/or bromine atoms, formyl-C₁-C₃-alkyl,        (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,        (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;        (C₁-C₃-haloalkyl)carbonyl-C₁-C₃-alkyl,        (C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to        7 fluorine, chlorine and/or bromine atoms,        (C₁-C₃-alkyl)carbonyl-C₁-C₃-haloalkyl,        (C₁-C₃-alkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to        6 fluorine, chlorine and/or bromine atoms,        (C₁-C₃-haloalkyl)carbonyl-C₁-C₃-haloalkyl,        (C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1        to 13 fluorine, chlorine and/or bromine atoms; —COR⁶, —CONR⁷R⁸        or —CH₂NR⁹R¹⁰,    -   R⁶, R⁷, R⁸, R⁹ and R¹⁰ are as defined above,    -   X⁶ represents chlorine, bromine or iodine,    -   in the presence of a base and in the presence of a diluent.

Finally, it has been found that the novel oxathiincarboxamides of theformula (I) have very good microbicidal properties and can be used forcontrolling unwanted microorganisms both in crop protection and in theprotection of materials.

Surprisingly, the oxathiincarboxamides of the formula (I) according tothe invention have considerably better fungicidal activity than theconstitutionally most similar active compounds of the prior art havingthe same direction of action.

If appropriate, the compounds according to the invention can be presentas mixtures of different possible isomeric forms, in particular ofstereoisomers, such as, for example, E and Z, threo and erythro and alsooptical isomers, and, if appropriate, also of tautomers. What is claimedare both the E and the Z isomers, and the threo and erythro and also theoptical isomers, any mixtures of these isomers, and the possibletautomeric forms.

The formula (I) provides a general definition of theoxathiincarboxamides according to the invention. Preferred radicaldefinitions of the formulae mentioned above and below are given below.These definitions apply both to the end products of the formula (I) and,correspondingly, to all intermediates.

-   G¹ preferably represents fluorine, chlorine, bromine, iodine,    trifluoromethyl, difluoromethyl or cyclopropyl.-   G¹ particularly preferably represents chlorine, bromine, iodine,    trifluoromethyl, difluoromethyl or cyclopropyl.-   G¹ very particularly preferably represents trifluoromethyl.-   G¹ also very particularly preferably represents difluoromethyl.-   G¹ also very particularly preferably represents cyclopropyl.-   G² preferably represents hydrogen.-   G² also preferably represents methyl.-   G³ preferably represents hydrogen.-   G³ also preferably represents methyl.-   G² and G³ particularly preferably both represent hydrogen.-   n preferably represents 0 or 2.-   n particularly preferably represents 0.-   n also particularly preferably represents 2.-   R¹ preferably represents hydrogen, fluorine, chlorine or methyl.-   R¹ particularly preferably represents hydrogen, fluorine or    chlorine.-   R¹ very particularly preferably represents hydrogen.-   R¹ also very particularly preferably represents fluorine.-   R² preferably represents hydrogen, fluorine, chlorine, isopropyl or    methylthio.-   R² particularly preferably represents hydrogen, fluorine, isopropyl    or methylthio.-   R² very particularly preferably represents hydrogen.-   R³ preferably represents hydrogen, fluorine, chlorine or methyl.-   R³ particularly preferably represents hydrogen or fluorine.-   R³ very particularly preferably represents hydrogen.-   R³ also very particularly preferably represents fluorine.-   R⁴ preferably represents hydrogen, fluorine, chlorine or methyl.-   R⁴ particularly preferably represents hydrogen or methyl.-   R⁴ very particularly preferably represents hydrogen.-   R⁴ also very particularly preferably represents methyl.-   R¹, R², R³ and R⁴ very particularly preferably all represent    hydrogen.-   R⁵ preferably represents hydrogen; C₁-C₆-alkyl, C₁-C₄-alkylsulfinyl,    C₁-C₄-alkyl-sulfonyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl;    C₁-C₄-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl,    C₁-C₄-haloalkylsulfonyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,    C₃-C₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms, formyl-C₁-C₃-alkyl,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;    (C₁-C₃-haloalkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 7    fluorine, chlorine and/or bromine atoms,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-haloalkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 6    fluorine, chlorine and/or bromine atoms,    (C₁-C₃-haloalkyl)carbonyl-C₁-C₃-haloalkyl,    (C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to    13 fluorine, chlorine and/or bromine atoms; —COR⁶, —CONR⁷R⁸ or    —CH₂NR⁹R¹⁰.-   R⁵ particularly preferably represents hydrogen, methyl, ethyl, n- or    isopropyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl,    methylsulfinyl, ethylsulfinyl, n- or isopropylsulfinyl, n-, iso-,    sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or    isopropylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl,    methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl,    cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl,    trifluoroethyl, difluoromethylthio, difluorochloromethylthio,    trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethyl    sulfonyl, trifluoromethoxymethyl,-    —CH₂—CHO, —CH₂CH₂—CHO, —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃,    —CH₂—CO—CH(CH₃)₂, —CH₂CH₂—CO—CH₃, —CH₂CH₂—CO—CH₂CH₃,    —CH₂CH₂—CO—CH(CH₃)₂, —CH₂—C(O)OCH₃, —CH₂—C(O)OCH₂CH₃,    —CH₂—C(O)OCH(CH₃)₂, —CH₂CH₂—C(O)OCH₃, —CH₂CH₂—C(O)OCH₂CH₃,    —CH₂CH₂—C(O)OCH(CH₃)₂, —CH₂—CO—CF₃, —CH₂—CO—CCl₃, —CH₂—CO—CH₂CF₃,    —CH₂—CO—CH₂CCl₃, —CH₂CH₂—CO—CH₂CF₃, —CH₂CH₂—CO—CH₂CCl₃,    —CH₂—C(O)OCH₂CF₃, —CH₂—C(O)OCF₂CF₃, —CH₂—C(O)OCH₂CCl₃,    —CH₂—C(O)OCCl₂CCl₃, —CH₂CH₂—C(O)OCH₂CF₃, —CH₂CH₂—C(O)OCF₂CF₃,    —CH₂CH₂—C(O)OCH₂CCl₃, —CH₂CH₂—C(O)O—CCl₂CCl₃; —COR⁶, —CONR⁷R⁸ or    —CH₂NR⁹R¹⁰.-   R⁵ very particularly preferably represents hydrogen; methyl,    methoxymethyl, —CH₂—CHO, —CH₂CH₂—CHO, —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃,    —CH₂—CO—CH(CH₃)₂ or —COR⁶.-   R⁶ preferably represents hydrogen, C₁-C₆-alkyl, C₁-C₄-alkoxy,    C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl; C₁-C₄-haloalkyl,    C₁-C₄-haloalkoxy, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,    C₃-C₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms, —COR¹¹.-   R⁶ particularly preferably represents hydrogen, methyl, ethyl, n- or    isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy,    cyclopropyl; trifluoromethyl, trifluoromethoxy, —COR¹¹.-   R⁶ very particularly preferably represents hydrogen, —COCH₃, —CHO,    —COCH₂OCH₃, —COCO₂CH₃, —COCO₂CH₂CH₃.-   R⁷ and R⁸ independently of one another preferably represent    hydrogen, C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl;    C₁-C₄-haloalkyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-halocycloalkyl    having in each case 1 to 9 fluorine, chlorine and/or bromine atoms.-   R⁷ and R⁸ furthermore together with the nitrogen to which they are    attached preferably represent a saturated heterocycle having 5 to 8    ring atoms, where the heterocycle may contain 1 or 2 further    nonadjacent heteroatoms from the group consisting of oxygen, sulfur    and NR¹² and is optionally mono- to tetrasubstituted by identical or    different substituents from the group consisting of halogen and    C₁-C₄-alkyl.-   R⁷ and R⁸ independently of one another particularly preferably    represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec-    or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl,    ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl,    trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.-   R⁷ and R⁸ furthermore together with the nitrogen atom to which they    are attached particularly preferably form a saturated heterocycle    from the group consisting of morpholine, thiomorpholine and    piperazine, where the piperazine may be substituted at the second    nitrogen atom by R¹², which heterocycle is optionally mono- to    tetra-substituted by identical or different substituents from the    group consisting of fluorine, chlorine, bromine and methyl.-   R⁹ and R¹⁰ independently of one another preferably represent    hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl; C₁-C₄-haloalkyl,    C₃-C₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms.-   R⁹ and R¹⁰ furthermore together with the nitrogen to which they are    attached preferably form a saturated heterocycle having 5 to 8 ring    atoms, where the heterocycle may contain 1 or 2 further nonadjacent    heteroatoms from the group consisting of oxygen, sulfur and NR¹² and    is optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen and C₁-C₄-alkyl.-   R⁹ and R¹⁰ independently of one another particularly preferably    represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec-    or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl,    ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl,    trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.-   R⁹ and R¹⁰ furthermore together with the nitrogen atom to which they    are attached particularly preferably form a saturated heterocycle    from the group consisting of morpholine, thiomorpholine and    piperazine, where the piperazine may be substituted at the second    nitrogen atom by R¹², which heterocycle is optionally mono- to    tetra-substituted by identical or different substituents from the    group consisting of fluorine, chlorine, bromine and methyl.-   R¹¹ preferably represents hydrogen, C₁-C₆-alkyl, C₁-C₄-alkoxy,    C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl; C₁-C₄-haloalkyl,    C₁-C₄-haloalkoxy, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,    C₃-C₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms.-   R¹¹ particularly preferably represents hydrogen, methyl, ethyl, n-    or isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy,    cyclopropyl; trifluoromethyl, trifluoromethoxy.-   R¹² preferably represents hydrogen or C₁-C₄-alkyl.-   R¹² particularly preferably represents hydrogen, methyl, ethyl, n-    or isopropyl, n-, iso-, sec- or tert-butyl.-   Z preferably represents Z¹.-   Z¹ preferably represents phenyl which is optionally mono- to    pentasubstituted by identical or different substituents, where the    substituents are selected from the list W¹.-   Z¹ particularly preferably represents monosubstituted phenyl, where    the substituents are selected from the list W¹.-   Z¹ also particularly preferably represents phenyl which is    disubstituted by identical or different substituents, where the    substituents are selected from the list W¹.-   Z¹ also particularly preferably represents phenyl which is    trisubstituted by identical or different substituents, where the    substituents are selected from the list W¹.-   Z¹ very particularly preferably represents phenyl which is    monosubstituted in the 4-position, where the substituents are    selected from the list W¹.-   Z¹ very particularly preferably represents phenyl which is    disubstituted by identical or different substituents in the    3,4-position, where the substituents are selected from the list W¹.-   Z¹ very particularly preferably represents phenyl which is    disubstituted by identical or different substituents in the    2,4-position, where the substituents are selected from the list W¹.-   Z¹ very particularly preferably represents phenyl which is    disubstituted by identical or different substituents in the    3,5-position, where the substituents are selected from the list W¹.-   Z¹ very particularly preferably represents phenyl which is    trisubstituted by identical or different substituents in the    2,4,6-position, where the substituents are selected from the list    W¹.-   W¹ represents halogen, cyano, nitro, amino, hydroxyl, formyl,    carboxyl, carbamoyl, thiocarbamoyl;-    in each case straight-chain or branched alkyl, hydroxyalkyl,    oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl,    alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 8    carbon atoms;-    in each case straight-chain or branched alkenyl or alkenyloxy    having in each case 2 to 6 carbon atoms;-    in each case straight-chain or branched haloalkyl, haloalkoxy,    haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having in each    case 1 to 6 carbon atoms and 1 to 13 identical or different halogen    atoms;-    in each case straight-chain or branched haloalkenyl or    haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11    identical or different halogen atoms;-    in each case straight-chain or branched alkylamino, dialkylamino,    alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl,    dialkylaminocarbonyl, arylalkylaminocarbonyl,    dialkylaminocarbonyloxy having 1 to 6 carbon atoms in the respective    hydrocarbon chains, alkenylcarbonyl or alkynylcarbonyl having 2 to 6    carbon atoms in the respective hydrocarbon chains;-    cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon    atoms;-    in each case doubly attached alkylene having 3 or 4 carbon atoms,    oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or    2 carbon atoms, each of which radicals is optionally mono- to    tetrasubstituted by identical or different substituents from the    group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl    and ethyl;-    or a grouping-    in which    -   Q¹ represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon        atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine,        chlorine and/or bromine atoms or cycloalkyl having 1 to 6 carbon        atoms and    -   Q² represents hydroxyl, amino, methylamino, phenyl, benzyl or        represents in each case optionally cyano-, hydroxyl-, alkoxy-,        alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted        alkyl or alkoxy having 1 to 4 carbon atoms, or represents        alkenyloxy or alkynyloxy having in each case 2 to 4 carbon        atoms,-    and also phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl,    cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy,    phenylalkylthio or heterocyclylalkyl having in each case 1 to 3    carbon atoms in the respective alkyl moieties, each of which    radicals is optionally mono- to trisubstituted in the cyclic part by    halogen and/or straight-chain or branched alkyl or alkoxy having 1    to 4 carbon atoms.-   W¹ preferably represents fluorine, chlorine, bromine, methyl, ethyl,    n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or    i-propoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy,    trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, in each    case doubly attached difluoromethylenedioxy or    tetrafluoroethylenedioxy,-    or a grouping-    where-    Q¹ represents hydrogen, methyl, ethyl or trifluoromethyl and-    Q² represents hydroxyl, methoxy, ethoxy, propoxy or isopropoxy.-   Z also preferably represents Z².-   Z² preferably represents cycloalkyl or bicycloalkyl having in each    case 3 to 10 carbon atoms, each of which radicals is optionally    mono- to tetrasubstituted by identical or different substituents    from the group consisting of halogen and C₁-C₄-alkyl.-   Z² particularly preferably represents cyclopropyl, cyclopentyl,    cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl,    bicyclo[2.2.1]heptyl or bicyclo[2.2.2]octyl, each of which is    optionally mono- to tetrasubstituted by identical or different    substituents from the group consisting of chlorine and methyl.-   Z² very particularly preferably represents cyclopropyl which is    substituted by chlorine and methyl.-   Z also preferably represents Z³.-   Z³ preferably represents unsubstituted C₂-C₂₀-alkyl or represents    C₁-C₂₀-alkyl which is mono- or polysubstituted by identical or    different substituents from the group consisting of fluorine,    chlorine, bromine, iodine and C₃-C₆-cycloalkyl, where the cycloalkyl    moiety for its part may be mono- to tetrasubstituted by identical or    different substituents from the group consisting of fluorine,    chlorine, bromine, iodine, C₁-C₄-alkyl and C₁-C₄-haloalkyl.-   Z³ particularly preferably represents unsubstituted C₂-C₂₀-alkyl.-   Z³ also particularly preferably represents C₁-C₂₀-alkyl which is    substituted by chlorine, cyclopropyl, dichlorocyclopropyl,    cyclobutyl, cyclopentyl or cyclohexyl.-   Z also preferably represents Z⁴.-   Z⁴ preferably represents C₂-C₂₀-alkenyl or C₂-C₂₀-alkynyl, each of    which is optionally mono- or polysubstituted by identical or    different substituents from the group consisting of fluorine,    chlorine, bromine, iodine and C₃-C₆-cycloalkyl, where the cycloalkyl    moiety for its part may optionally be mono- to tetrasubstituted by    identical or different substituents from the group consisting of    fluorine, chlorine, bromine, iodine, C₁-C₄-alkyl and    C₁-C₄-haloalkyl.-   Z⁴ particularly preferably represents C₂-C₂₀-alkenyl or    C₂-C₂₀-alkynyl.-   Z and R⁴ also preferably together with the carbon atoms to which    they are attached represent a 5- or 6-membered carbocyclic or    heterocyclic ring which is optionally mono- to tetrasubstituted by    identical or different substituents.-   Z and R⁴ also particularly preferably together with the carbon atoms    to which they are attached represent a 5- or 6-membered carbocyclic    ring which is optionally mono-, di- or trisubstituted by methyl.

Preferred are those compounds of the formula (I) in which all radicalseach have the preferred meanings mentioned above.

Particular preference is given to those compounds of the formula (I) inwhich all radicals each have the particularly preferred meaningsmentioned above.

Preference is furthermore given to compounds of the formula (Ic)

in whichG¹, G², G³, n, R¹, R², R³, R⁴ and Z¹ are as defined above.

Particular preference is given to compounds of the formula (Ic) in whichG¹ represents trifluoromethyl.

Particular preference is given to compounds of the formula (Ic) in whichG¹ represents difluoromethyl.

Particular preference is given to compounds of the formula (Ic) in whichR¹, R², R³ and R⁴ each represent hydrogen.

Particular preference is given to compounds of the formula (Ic) in whichn represents 0.

Preference is furthermore given to compounds of the formula (Id)

in whichG¹, G², G³, n, R¹, R², R³, R⁴ and Z² are as defined above.

Particular preference is given to compounds of the formula (Id) in whichG¹ represents trifluoromethyl.

Particular preference is given to compounds of the formula (Id) in whichG¹ represents difluoromethyl.

Particular preference is given to compounds of the formula (Id) in whichR¹, R², R³ and R⁴ each represent hydrogen.

Particular preference is given to compounds of the formula (Id) in whichn represents 0.

Preference is furthermore given to compounds of the formula (Ie)

in whichG¹, G², G³, n, R¹, R², R³, R⁴ and Z³ are as defined above.

Particular preference is given to compounds of the formula (Ie) in whichG¹ represents trifluoromethyl.

Particular preference is given to compounds of the formula (Ie) in whichG¹ represents difluoromethyl.

Particular preference is given to compounds of the formula (Ie) in whichR¹, R², R³ and R⁴ each represent hydrogen.

Particular preference is given to compounds of the formula (Ie) in whichn represents 0.

Preference is furthermore given to compounds of the formula (If)

in whichG¹, G², G³, n, R¹, R², R³, R⁴ and Z⁴ are as defined above.

Particular preference is given to compounds of the formula (If) in whichG¹ represents trifluoromethyl.

Particular preference is given to compounds of the formula (If) in whichG¹ represents difluoromethyl.

Particular preference is given to compounds of the formula (If) in whichR¹, R², R³ and R⁴ each represent hydrogen.

Particular preference is given to compounds of the formula (If) in whichn represents 0.

Preference is furthermore given to compounds of the formula (Ig)

in whichG¹, G², G³, n, R¹, R², R³, R⁴, R⁵⁻¹ and Z are as defined above.

-   R⁵⁻¹ preferably represents C₁-C₆-alkyl, C₁-C₄-alkylsulfinyl,    C₁-C₄-alkylsulfonyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl;    C₁-C₄-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl,    C₁-C₄-haloalkylsulfonyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,    C₃-C₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms, formyl-C₁-C₃-alkyl,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;    (C₁-C₃-haloalkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 7    fluorine, chlorine and/or bromine atoms,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-haloalkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 6    fluorine, chlorine and/or bromine atoms,    (C₁-C₃-haloalkyl)carbonyl-C₁-C₃-haloalkyl,    (C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to    13 fluorine, chlorine and/or bromine atoms; —COR⁶, —CONR⁷R⁸ or    —CH₂NR⁹R¹⁰.-   R⁵⁻¹ particularly preferably represents methyl, ethyl, n- or    isopropyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl,    methylsulfinyl, ethylsulfinyl, n- or isopropylsulfinyl, n-, iso-,    sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or    isopropylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl,    methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl,    cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl,    trifluoroethyl, difluoromethylthio, difluorochloromethylthio,    trifluoromethylthio, trifluoromethylsulfinyl,    trifluoromethylsulfonyl, trifluoromethoxymethyl, —CH₂—CHO,    —CH₂CH₂—CHO, —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂,    —CH₂CH₂—CO—CH₃, —CH₂CH₂—CO—CH₂CH₃, —CH₂CH₂—CO—CH(CH₃)₂,    —CH₂—C(O)OCH₃, —CH₂—C(O)OCH₂CH₃, —CH₂—C(O)OCH(CH₃)₂,    —CH₂CH₂—C(O)OCH₃, —CH₂CH₂—C(O)OCH₂CH₃, —CH₂CH₂—C(O)OCH(CH₃)₂,    —CH₂—CO—CF₃, —CH₂—CO—CCl₃, —CH₂—CO—CH₂CF₃, —CH₂—CO—CH₂CCl₃,    —CH₂CH₂—CO—CH₂CF₃, —CH₂CH₂—CO—CH₂CCl₃, —CH₂—C(O)OCH₂CF₃,    —CH₂—C(O)OCF₂CF₃, —CH₂—C(O)OCH₂CCl₃, —CH₂—C(O)OCCl₂CCl₃,    —CH₂CH₂—C(O)OCH₂CF₃, —CH₂CH₂—C(O)OCF₂CF₃, —CH₂CH₂—C(O)OCH₂CCl₃,    —CH₂CH₂—C(O)O—CCl₂CCl₃; —COR⁶, —CONR⁷R⁸ or —CH₂NR⁹R¹⁰.-   R⁵⁻¹ very particularly preferably represents methyl, methoxymethyl,    —CH₂—CHO, —CH₂CH₂—CHO, —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂    or —COR⁶.

Particular preference is given to compounds of the formula (Ig) in whichG¹ represents trifluoromethyl.

Particular preference is given to compounds of the formula (Ig) in whichG¹ represents difluoromethyl.

Particular preference is given to compounds of the formula (Ig) in whichR¹, R², R³ and R⁴ each represent hydrogen.

Particular preference is given to compounds of the formula (Ig) in whichn represents 0.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy.

The definition C₁-C₂₀-alkyl embraces the widest range defined here foran alkyl radical. Specifically, this definition includes the meaningsmethyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl, and in eachcase all isomeric pentyls, hexyls, heptyls, octyls, nonyls, decyls,undecyls, dodecyls, tridecyls, tetradecyls, pentadecyls, hexadecyls,heptadecyls, octadecyls, nonadecyls and eicosyls.

The definition C₂-C₂₀-alkenyl embraces the widest range defined here foran alkenyl radical. Specifically, this definition includes the meaningsethenyl, n-, isopropenyl, n-, iso-, sec-, tert-butenyl, and in each caseall isomeric pentenyls, hexenyls, heptenyls, octenyls, nonenyls,decenyls, undecenyls, dodecenyls, tridecenyls, tetradecenyls,pentadecenyls, hexadecenyls, heptadecenyls, octadecenyls, nonadecenylsand eicosenyls.

The definition C₂-C₂₀-alkynyl embraces the widest range defined here foran alkynyl radical. Specifically, this definition includes the meaningsethynyl, n-, isopropynyl, n-, iso-, sec-, tert-butynyl, and in each caseall isomeric pentynyls, hexynyls, heptynyls, octynyls, nonynyls,decynyls, undecynyls, dodecynyls, tridecynyls, tetradecynyls,pentadecynyls, hexadecynyls, heptadecynyls, octadecynyls, nonadecynylsand eicosynyls.

Optionally substituted radicals may be mono- or polysubstituted, wherein the case of polysubstitution the substituents can be identical ordifferent.

Halogen-substituted radicals, such as, for example, haloalkyl, are mono-or polyhalogenated. In the case of polyhalogenation, the halogen atomscan be identical or different. Here, halogen denotes fluorine, chlorine,bromine and iodine, in particular fluorine, chlorine and bromine.

The general or preferred radical definitions or illustrations givenabove can be combined between the respective ranges and preferred rangesas desired. The definitions apply both to the end products and,correspondingly, to precursors and intermediates.

Explanation of the Processes and Intermediates:

Process (a)

Using 6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carbonyl chloride and4′-chloro-2′-fluoro-1,1′-biphenyl-2-amine as starting materials, thecourse of the process (a) according to the invention can be illustratedby the formula scheme below.

The formula (II) provides a general definition of the oxathiincarboxylicacid derivatives required as starting materials for carrying out theprocess (a) according to the invention. In this formula (II), G¹, G², G³and n preferably, particularly preferably and very particularlypreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferredand very particularly preferred, respectively, for G¹, G², G³ and n. X¹preferably represents chlorine or hydroxyl.

Most of the starting materials of the formula (II) are known, and/or canbe prepared by known processes (cf. Han'guk Nonghwa Hakhoechi 2001, 44,191-196). Novel compounds of the formula (II) and processes for theirpreparation can be found in the Preparation Examples.

Compounds of the formula (II) in which n represents 1 or 2 are obtainedfrom the corresponding compounds in which n represents 0 by customaryoxidation methods, for example by reaction with hydrogen peroxide (H₂O₂)in the presence of formic acid and a diluent (for example4-methyl-2-pentanone). The degree of oxidation can in each case becontrolled via the reaction conditions.

In the same manner, it is also possible to oxidize compounds of theformula (I) in which n represents 0, giving compounds of the formula (I)in which n represents 1 or 2. The degree of oxidation can in each casebe controlled by the reaction conditions.

The formula (III) provides a general definition of the anilinederivatives furthermore required as starting materials for carrying outthe process (a) according to the invention. In this formula (III), R¹,R², R³, R⁴, R⁵ and Z preferably, particularly preferably and veryparticularly preferably have those meanings which have already beenmentioned in connection with the description of the compounds of theformula (I) according to the invention as being preferred, particularlypreferred and very particularly preferred, respectively, for theseradicals.

Most of the starting materials of the formula (III) are known, and/orcan be prepared by known processes (cf., for example, Bull. Korean Chem.Soc. 2000 21, 165-166; Chem. Pharm. Bull. 1992, 40, 240-244;Heterocycles 1989, 29, 1013-1016; J. Med. Chem. 1996, 39, 892-903;Synthesis 1995, 713-16; Synth. Commun. 1994, 24, 267-272; Synthesis1994, 142-144; DE-A 27 27 416; EP-A 0 824 099; WO 93/11117, EP-A 0 545099, EP-A 0 589 301, EP-A 0 589 313 and WO 02/38542).

It is also possible to initially prepare aniline derivatives of theformula (III) in which R⁵ represents hydrogen and then to derivatize thecompounds obtained in this manner using customary methods [for exampleanalogously to the process (i) according to the invention].

Novel compounds of the formula (III) and processes for their preparationcan be found in the Preparation Examples.

Process (b)

UsingN-(2-bromophenyl)-6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxamideand 4-chloro-2-fluorophenylboronic acid as starting materials and acatalyst, the course of the process (b) according to the invention canbe illustrated by the formula scheme below.

The formula (IV) provides a general definition of thehalooxathiincarboxamides required as starting materials for carrying outthe process (b) according to the invention. In this formula (IV), G¹,G², G³, n, R¹, R², R³, R⁴ and R⁵ preferably, particularly preferably andvery particularly preferably have those meanings which have already beenmentioned in connection with the description of the compounds of theformula (I) according to the invention as being preferred, particularlypreferred and very particularly preferred, respectively, for theseradicals and this index. X² represents bromine or iodine.

The halooxathiincarboxamides of the formula (IV) have hitherto not beendisclosed. As novel chemical compounds, they also form part of thesubject-matter of the present application. They are obtained whenj) oxathiincarboxylic acid derivatives of the formula (II)

-   -   in which    -   G¹, G², G³ and n are as defined above and    -   X¹ represents halogen or hydroxyl,    -   are reacted with haloanilines of the formula (XIV)    -   in which    -   R¹, R², R³, R⁴, R⁵ and X² are as defined above,    -   if appropriate in the presence of a catalyst, if appropriate in        the presence of a condensing agent, if appropriate in the        presence of an acid binder and if appropriate in the presence of        a diluent.        Process (j)

Using 6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carbonyl chloride and2-bromoaniline as starting materials, the course of the process (j)according to the invention can be illustrated by the formula schemebelow.

The oxathiincarbonyl halides of the formula (II) required as startingmaterials for carrying out the process (j) according to the inventionhave already been described further above, in connection with theprocess (a) according to the invention.

The formula (XIV) provides a general definition of the haloanilinesfurthermore required as starting materials for carrying out the process(j) according to the invention. In this formula (XIV), R¹, R², R³, R⁴,R⁵ and X² preferably, particularly preferably and very particularlypreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention or of the precursors of the formula (III) asbeing preferred, particularly preferred and very particularly preferred,respectively, for these radicals.

The haloanilines of the formula (XIV) are commercial chemicals forsynthesis or can be obtained by known processes. If R⁵ does notrepresent hydrogen, the radical R⁵ can be introduced at the stage of thecompounds of the formula (XIV) using customary derivatization methods.It is also possible to initially prepare compounds of the formula (IV)in which R⁵ represents hydrogen and then to derivatize the resultingproducts by customary methods [cf. the process (i) according to theinvention].

The formula (V) provides a general definition of the boronic acidderivatives furthermore required as starting materials for carrying outthe process (b) according to the invention. In this formula (V), Z¹preferably, particularly preferably and very particularly preferably hasthose meanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively, for Z¹. A¹ and A² each representhydrogen or together represent tetramethylethylene.

The boronic acid derivatives of the formula (V) are known and/or can beprepared by known processes (cf., for example, WO 01/90084 and U.S. Pat.No. 5,633,218).

Process c)

Using2-{[6-(trifluoromethyl)-2,3-dihydro-1,4-oxathiin-5-yl]carbonylamino}phenylboronicacid and 1-bromo-4-chloro-2-fluorobenzene as starting materials and acatalyst, the course of the process (c) according to the invention canbe illustrated by the formula scheme below.

The formula (VI) provides a general definition of theoxathiincarboxamideboronic acid derivatives required as startingmaterials for carrying out the process (c) according to the invention.In this formula (VI), G¹, G², G³, n, R¹, R², R³, R⁴ and R⁵ preferably,particularly preferably and very particularly preferably have thosemeanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively for these radicals and this index.A³ and A⁴ each represent hydrogen or together representtetramethylethylene.

The oxathiincarboxamideboronic acid derivatives of the formula (VI) havehitherto not been disclosed. They are novel chemical compounds and alsoform part of the subject-matter of the present application. They areobtained whenk) an oxathiincarboxylic acid derivative of the formula (II)

-   -   in which    -   G¹, G², G³ and n are as defined above and    -   X¹ represents halogen or hydroxyl    -   is reacted with an anilineboronic acid derivative of the formula        (XV)    -   in which    -   R¹, R², R³, R⁴, R⁵, A³ and A⁴ are as defined above,    -   if appropriate in the presence of a catalyst, if appropriate in        the presence of a condensing agent, if appropriate in the        presence of an acid binder and if appropriate in the presence of        a diluent.        Process (k)

Using 6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carbonyl chloride and2-amino-phenylboronic acid as starting materials, the course of theprocess (k) according to the invention can be illustrated by the formulascheme below.

The oxathiincarboxylic acid derivatives of the formula (II) required asstarting materials for carrying out the process (k) according to theinvention have already been described further above, in connection withthe process (a) according to the invention.

The formula (XV) provides a general definition of the anilineboronicacid derivatives furthermore required as starting materials for carryingout the process (k) according to the invention. In this formula (XV),R¹, R², R³, R⁴ and R⁵ preferably, particularly preferably and veryparticularly preferably have those meanings which have already beenmentioned in connection with the description of the compounds of theformula (I) according to the invention as being preferred, particularlypreferred and very particularly preferred, respectively, for theseradicals. A³ and A⁴ each represent hydrogen or together representtetramethylethylene.

The anilineboronic acid derivatives of the formula (XV) are knownchemicals for synthesis or can be obtained by known processes. If R⁵does not represent hydrogen, the radical R⁵ can be introduced at thestage of the compounds of the formula (XV) using customaryderivatization methods. It is also possible to initially preparecompounds of the formula (VI) in which R⁵ represents hydrogen and thento derivatize the products obtained using customary methods [cf. theprocess (i) according to the invention].

The formula (VII) provides a general definition of the phenylderivatives furthermore required as starting materials for carrying outthe process (c) according to the invention. In this formula (VII), Z¹preferably, particularly preferably and very particularly preferably hasthose meanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively, for Z¹. X³ represents chlorine,bromine, iodine or trifluoromethylsulfonate.

The phenyl derivatives of the formula (VII) are known chemicals forsynthesis.

Process d)

UsingN-(2-bromophenyl)-6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxamideand 1-bromo-4-chloro-2-fluorobenzene as starting materials and acatalyst and4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, the courseof the process (d) according to the invention can be illustrated by theformula scheme below.

The halooxathiincarboxamides of the formula (IV) and the phenylderivatives of the formula (VII) required as starting materials forcarrying out the process (d) according to the invention have alreadybeen described further above, in connection with the processes (b) and(c) according to the invention.

The 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolanefurthermore required for carrying out the process (d) according to theinvention is a commercial chemical for synthesis.

Process e)

If, for example,N-[2-(1,3-dimethylbut-1-enyl)phenyl][6-(trifluoromethyl)(2,3-dihydro-1,4-oxathiin-5-yl)]carboxamideis hydrogenated, the course of the process (e) according to theinvention can be illustrated by the formula scheme below.

The formula (Ia) provides a general definition of theoxathiincarboxamides required as starting materials for carrying out theprocess (e) according to the invention. In this formula (Ia), G¹, G²,G³, n, R¹, R², R³ and R⁴ preferably, particularly preferably and veryparticularly preferably have those meanings which have already beenmentioned in connection with the description of the compounds of theformula (I) according to the invention as being preferred, particularlypreferred and very particularly preferred, respectively, for theseradicals and this index.

-   X⁴ preferably represents C₂-C₂₀-alkenyl or C₂-C₂₀-alkynyl, each of    which is optionally mono- or polysubstituted by identical or    different substituents from the group consisting of fluorine,    chlorine, bromine, iodine and C₃-C₆-cycloalkyl, where the cycloalkyl    moiety for its part may optionally be mono- to tetrasubstituted by    identical or different substituents from the group consisting of    fluorine, chlorine, bromine, iodine, C₁-C₄-alkyl and    C₁-C₄-haloalkyl.-   X⁴ particularly preferably represents C₂-C₂₀-alkenyl or    C₂-C₂₀-alkynyl.

The compounds of the formula (Ia) are compounds according to theinvention and can be prepared according to processes (a), (f), (g) or(h).

Process (f)

If, for example,N-[2-(1-hydroxy-1,3-dimethylbutyl)phenyl][6-(trifluoromethyl)(2,3-dihydro-1,4-oxathiin-5-yl)]carboxamideis dehydrated, the course of the process (f) according to the inventioncan be illustrated by the formula scheme below.

The formula (VIII) provides a general definition of thehydroxyalkyloxathiincarboxamides required as starting materials forcarrying out the process (f) according to the invention. In this formula(VIII), G¹, G², G³, n, R¹, R², R³, R⁴ and R⁵ preferably, particularlypreferably and very particularly preferably have those meanings whichhave already been mentioned in connection with the description of thecompounds of the formula (I) according to the invention as beingpreferred, particularly preferred and very particularly preferred,respectively, for these radicals and this index.

-   X⁵ preferably represents C₂-C₁₂-hydroxyalkyl which is optionally    additionally mono- to tetrasubstituted by identical or different    substituents from the group consisting of chlorine, fluorine,    bromine and/or C₃-C₆-cycloalkyl, where the cycloalkyl moiety for its    part may optionally be substituted by halogen and/or C₁-C₄-alkyl.-   X⁵ particularly preferably represents in each case straight-chain or    branched hydroxy-ethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl,    hydroxyhexyl, hydroxyheptyl, hydroxyoctyl, hydroxynonyl or    hydroxydecyl, each of which may be attached in any position and each    of which is optionally mono- to tetrasubstituted by identical or    different substituents from the group consisting of fluorine,    cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and    cyclohexyl.

The compounds of the formula (VIII) have hitherto not been disclosedand, as novel compounds, also form part of the subject-matter of thepresent application.

It has also been found that the hydroxyalkylpyrazolylcarboxamides of theformula (VIII) have very good microbicidal properties and can be usedfor controlling unwanted micro-organisms both in crop protection and inthe protection of materials.

The hydroxyalkylpyrazolylcarboxamides of the formula (VIII) are obtainedwhenl) oxathiincarboxylic acid derivatives of the formula (II)

-   -   in which    -   G¹, G², G³ and n are as defined above and    -   X¹ represents halogen or hydroxyl,    -   are reacted with a hydroxyalkylaniline derivative of the formula        (XVI)    -   in which    -   R¹, R², R³, R⁴, R⁵ and X⁵ are as defined above,    -   if appropriate in the presence of a catalyst, if appropriate in        the presence of a condensing agent, if appropriate in the        presence of an acid binder and if appropriate in the presence of        a diluent.        Process (l)

Using, for example,6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carbonyl chloride and2-(2-aminophenyl)-2-heptanol as starting materials, the course of theprocess (1) according to the invention can be illustrated by the formulascheme below:

The oxathiincarboxylic acid derivatives of the formula (II) required asstarting materials for carrying out the process (l) according to theinvention have already been described further above, in connection withthe process (a) according to the invention.

The formula (XVI) provides a general definition of thehydroxyalkylaniline derivatives furthermore required as startingmaterials for carrying out the process (l) according to the invention.In this formula (XVI), R¹, R², R³, R⁴, R⁵ and X⁵ preferably,particularly preferably and very particularly preferably have thosemeanings which have already been mentioned in connection with thedescription of the compounds of the formulae (I) and (VIII) according tothe invention as being preferred, particularly preferred and veryparticularly preferred, respectively, for these radicals.

The hydroxyalkylaniline derivatives of the formula (XVI) are knownand/or can be obtained by known methods (cf., for example, U.S. Pat. No.3,917,592 or EP-A 0 824 099). If R⁵ does not represent hydrogen, theradical R⁵ can be introduced at the stage of the compounds of theformula (XVI) using customary derivatization methods. It is alsopossible to initially prepare compounds of the formula (VIII) in whichR⁵ represents hydrogen and then to derivatize the products obtainedusing customary methods [cf. the process (i) according to theinvention].

Process (g)

Using, for example,N-(2-bromophenyl)-6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxamideand 1-hexyne as starting materials and a catalyst, the course of theprocess (g) according to the invention can be illustrated by the formulascheme below.

The halooxathiincarboxamides of the formula (IV) required as startingmaterials for carrying out the process (g) according to the inventionhave already been described further above, in connection with theprocess (c) according to the invention.

The formula (IX) provides a general definition of the alkynesfurthermore required as starting materials for carrying out the process(g) according to the invention.

-   A⁵ preferably represents C₂-C₁₀-alkyl which is optionally mono- to    tetrasubstituted by identical or different substituents from the    group consisting of fluorine, chlorine, bromine and    C₃-C₆-cycloalkyl, where the cycloalkyl moiety for its part may    optionally be substituted by halogen and/or C₁-C₄-alkyl.-   A⁵ particularly preferably represents in each case straight-chain or    branched ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, each    of which may be attached in any position and each of which is    optionally mono- to tetrasubstituted by identical or different    substituents from the group consisting of fluorine, cyclopropyl,    difluorocyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The alkynes of the formula (VI) are known chemicals for synthesis.

The formula (X) provides a general definition of the alkenes furthermorealternatively required as starting materials for carrying out theprocess (g) according to the invention.

-   A⁶, A⁷ and A⁸ independently of one another preferably each represent    hydrogen or alkyl which is optionally mono- to tetrasubstituted by    identical or different substituents from the group consisting of    fluorine, chlorine, bromine and C₃-C₆-cycloalkyl, where the    cycloalkyl moiety for its part may optionally be substituted by    halogen and/or C₁-C₄-alkyl and where the total number of carbon    atoms of the open-chain part of the molecule does not exceed the    number 12.-   A⁶, A⁷ and A⁸ independently of one another particularly preferably    each represent hydrogen or in each case straight-chain or branched    ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, each of which    may be attached in any position and each of which is optionally    mono- to tetrasubstituted by identical or different substituents    from the group consisting of fluorine, cyclopropyl,    difluorocyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, where    the total number of the carbon atoms of the open-chain part of the    molecule does not exceed the number 12.

The alkenes of the formula (VII) are known chemicals for synthesis.

Process (h)

UsingN-(2-acetylphenyl)[6-(trifluoromethyl)(2,3-dihydro-1,4-oxathiin-5-yl)]carboxamideand butyl(triphenyl)phosphonium iodide as starting materials, the courseof the process (h) according to the invention can be illustrated by theformula scheme below:

The formula (XI) provides a general definition of the ketones requiredas starting materials for carrying out the process (h) according to theinvention. In this formula, G¹, G², G³, n, R¹, R², R³, R⁴ and R⁵preferably, particularly preferably and very particularly preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) according to theinvention as being preferred, particularly preferred and veryparticularly preferred, respectively, for these radicals and this index.

-   A⁹ preferably represents C₂-C₁₀-alkyl which is optionally mono- to    tetrasubstituted by identical or different substituents from the    group consisting of fluorine, chlorine, bromine and    C₃-C₆-cycloalkyl, where the cycloalkyl moiety for its part may    optionally be substituted by halogen and/or C₁-C₄-alkyl.-   A⁹ particularly preferably represents in each case straight-chain or    branched ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, each    of which may be attached in any position and each of which is    optionally mono- to tetrasubstituted by identical or different    substituents from the group consisting of fluorine, cyclopropyl,    difluoro-cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The ketones of the formula (XI) have hitherto not been disclosed. Asnovel chemical compounds, they also form part of the subject-matter ofthe present application. They are obtained whenm) oxathiincarboxylic acid derivatives of the formula (II)

-   -   in which    -   G¹, G², G³ and n are as defined above and    -   X¹ represents halogen or hydroxyl    -   are reacted with ketoanilines of the formula (XVII)    -   in which    -   R¹, R², R³, R⁴, R⁵ and A⁹ are as defined above,    -   if appropriate in the presence of a catalyst, if appropriate in        the presence of a condensing agent, if appropriate in the        presence of an acid binder and if appropriate in the presence of        a diluent.        Process (m)

Using 6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carbonyl chloride and1-(2-amino-phenyl)ethanone as starting materials, the course of theprocess (m) according to the invention can be illustrated by the formulascheme below:

The oxathiincarboxylic acid derivatives of the formula (II) required asstarting materials for carrying out the process (m) according to theinvention have already been described further above, in connection withthe process a) according to the invention.

The formula (XVII) provides a general definition of the ketoanilinesfurthermore required as starting materials for carrying out the process(m) according to the invention. In this formula (XVII), R¹, R², R³, R⁴,R⁵ and A⁹ preferably, particularly preferably and very particularlypreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formulae (I) and(XI) according to the invention as being preferred, particularlypreferred and very particularly preferred, respectively, for theseradicals.

The ketoanilines of the formula (XII) are generally customary chemicalsfor synthesis (cf., for example, J. Am. Chem. Soc. 1978, 100, 4842-4857or U.S. Pat. No. 4,032,573). If R⁵ does not represent hydrogen, theradical R⁵ can be introduced at the stage of the compounds of theformula (XVII) using customary derivatization methods. It is alsopossible to initially prepare compounds of the formula (XI) in which R⁵represents hydrogen and then to derivatize the products obtained usingcustomary methods [cf. the process (i) according to the invention].

The formula (XII) provides a general definition of the phosphoruscompounds furthermore required as starting materials for carrying outthe process (h) according to the invention.

-   A¹⁰ preferably represents C₂-C₁₀-alkyl which is optionally mono- to    tetrasubstituted by identical or different substituents from the    group consisting of chlorine, fluorine, bromine and    C₃-C₆-cycloalkyl, where the cycloalkyl moiety for its part may    optionally be substituted by halogen and/or C₁-C₄-alkyl.-   A¹⁰ particularly preferably represents in each case straight-chain    or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl,    each of which may be attached in any position and each of which is    optionally mono- to tetrasubstituted by identical or different    substituents from the group consisting of fluorine, cyclopropyl,    difluoro-cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.-   Px preferably represents a grouping —P⁺(C₆H₅)₃Cl⁻, —P⁺(C₆H₅)₃Br⁻,    —P⁺(C₆H₅)₃I⁻, —P(═O)(OCH₃)₃ or —P(═O)(OC₂H₅)₃.

The phosphorus compounds of the formula (XII) are known and/or can beprepared by known processes (cf., for example, Justus Liebigs Ann. Chem.1953, 580, 44-57 or Pure Appl. Chem. 1964, 9, 307-335).

Process (i)

UsingN-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)-5,6-dihydro-1,4-oxathiin-3-carboxamideand acetyl chloride as starting materials, the course of the process (i)according to the invention can be illustrated by the formula schemebelow:

The formula (Ib) provides a general definition of theiodopyrazolylcarboxanilides required as starting materials for carryingout the process (i) according to the invention. In this formula (Ib),G¹, G², G³, n, R¹, R², R³, R⁴ and Z preferably, particularly preferablyand very particularly preferably have those meanings which have alreadybeen mentioned in connection with the description of the compounds ofthe formula (I) according to the invention as being preferred,particularly preferred and very particularly preferred, respectively,for these radicals and this index.

The compounds of the formula (Ib) are compounds according to theinvention and can be prepared according to processes (a) to (h).

The formula (XIII) provides a general definition of the halidesfurthermore required as starting materials for carrying out the process(i) according to the invention. In this formula (XIII), R⁵⁻¹ preferably,particularly preferably and very particularly preferably has thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (Ig) as being preferred,particularly preferred and very particularly preferred for theseradicals. X⁶ represents chlorine, bromine or iodine.

Halides of the formula (XIII) are known.

Reaction Conditions

Suitable diluents for carrying out the processes (a), (j), (k), (l) and(m) according to the invention are all inert organic solvents. Thesepreferably include aliphatic, alicyclic or aromatic hydrocarbons, suchas, for example, petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; halogenatedhydrocarbons, such as, for example, chlorobenzene, dichlorobenzene,dichloromethane, chloroform, carbon tetrachloride, dichloroethane ortrichloroethane; ethers, such as diethyl ether, diisopropyl ether,methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones, such asacetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles,such as acetonitrile, propionitrile, n- or i-butyronitrile orbenzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; mixtures thereof with water or purewater.

The processes (a), (j), (k), (l) and (m) according to the invention are,if appropriate, carried out in the presence of a suitable acid acceptor.Suitable acid acceptors are all customary inorganic or organic bases.These preferably include alkaline earth metal or alkali metal hydrides,hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates,such as, for example, sodium hydride, sodium amide, lithiumdiisopropylamide, sodium methoxide, sodium ethoxide, potassiumtert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate,sodium carbonate, potassium carbonate, potassium bicarbonate, sodiumbicarbonate or ammonium carbonate, and also tertiary amines, such astrimethylamine, triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methyl-piperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

The processes (a), (j), (k), (l) and (m) according to the invention are,if appropriate, carried out in the presence of a suitable condensingagent. Suitable condensing agents are all condensing agents which arecustomarily used for such amidation reactions. Examples which may bementioned are acid halide formers, such as phosgene, phosphorustribromide, phosphorus trichloride, phosphorus pentachloride, phosphorusoxychloride or thionyl chloride; anhydride formers, such as ethylchloroformate, methyl chloroformate, isopropyl chloroformate, isobutylchloroformate or methanesulfonyl chloride; carbodiimides, such asN,N′-dicyclohexylcarbodiimide (DCC), or other customary condensingagents, such as phosphorus pentoxide, polyphosphoric acid,N,N′-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline(EEDQ), triphenylphosphine/carbon tetrachloride orbromotripyrrolidinophosphonium hexafluorophosphate.

The processes (a), (j), (k), (l) and (m) according to the invention are,if appropriate, carried out in the presence of a catalyst. Exampleswhich may be mentioned are 4-dimethyl-aminopyridine,1-hydroxybenzotriazole and dimethylformamide.

When carrying out the processes (a), (j), (k), (l) and (m) according tothe invention, the reaction temperatures can be varied within arelatively wide range. In general, the processes are carried out attemperatures of from 0° C. to 150° C., preferably at temperatures offrom 0° C. to 80° C.

For carrying out the process (a) according to the invention forpreparing the compounds of the formula (I), in general from 0.8 to 15mol, preferably from 0.8 to 8 mol, of aniline derivative of the formula(III) are employed per mole of the oxathiincarboxylic acid derivative ofthe formula (II).

For carrying out the process (j) according to the invention forpreparing the compounds of the formula (IV), in general from 0.8 to 15mol, preferably from 0.8 to 8 mol, of haloaniline of the formula (XIV)are employed per mole of the oxathiincarboxylic acid derivative of theformula (II).

For carrying out the process (k) according to the invention forpreparing the compounds of the formula (VI), in general from 0.8 to 15mol, preferably from 0.8 to 8 mol, of aniline-boronic acid derivative ofthe formula (XV) are employed per mole of the oxathiincarboxylic acidderivative of the formula (II).

For carrying out the process (l) according to the invention forpreparing the compounds of the formula (VIII), in general from 0.8 to 15mol, preferably from 0.8 to 8 mol, of hydroxyalkylaniline derivative ofthe formula (XVI) are employed per mole of the oxathiincarboxylic acidderivative of the formula (II).

For carrying out the process (m) according to the invention forpreparing the compounds of the formula (IX), in general from 0.8 to 15mol, preferably from 0.8 to 8 mol, of ketoaniline of the formula (XVII)are employed per mole of the oxathiincarboxylic acid derivative of theformula (II).

Suitable diluents for carrying out the processes (b), (c) and (d)according to the invention are all inert organic solvents. Thesepreferably include aliphatic, alicyclic or aromatic hydrocarbons, suchas, for example, petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; ethers, such asdiethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethaneor anisole; nitriles, such as acetonitrile, propionitrile, n- ori-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate; sulfoxides, such as dimethyl sulfoxide; sulfones, such assulfolane; alcohols, such as methanol, ethanol, n- or i-propanol, n-,i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol,methoxyethanol, diethylene glycol monomethyl ether, diethylene glycolmonoethyl ether, mixtures thereof with water or pure water.

When carrying out the processes (b), (c) and (d) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperatures offrom 0° C. to 180° C., preferably at temperatures of from 20° C. to 150°C.

The processes (b), (c) and (d) according to the invention are, ifappropriate, carried out in the presence of a suitable acid acceptor.Suitable acid acceptors are all customary inorganic or organic bases.These preferably include alkaline earth metal or alkali metal hydrides,hydroxides, amides, alkoxides, acetates, fluorides, phosphates,carbonates or bicarbonates, such as, for example, sodium hydride, sodiumamide, lithium diisopropylamide, sodium methoxide, sodium ethoxide,potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodiumacetate, sodium phosphate, potassium phosphate, potassium fluoride,cesium fluoride, sodium carbonate, potassium carbonate, potassiumbicarbonate, sodium bicarbonate or cesium carbonate, and also tertiaryamines, such as trimethylamine, triethylamine, tributylamine,N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine,N-methylpiperidine, N-methyl-morpholine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloundecene (DBU).

The processes (b), (c) and (d) according to the invention are carriedout in the presence of a catalyst, such as, for example, a palladiumsalt or complex. Suitable catalysts are, preferably, palladium chloride,palladium acetate, tetrakis(triphenylphosphine)palladium,bis-triphenyl-phosphine)palladiumdichloride or1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride.

It is also possible to generate a palladium complex in the reactionmixture by separately adding a palladium salt and a complex ligand, suchas, for example, triethylphosphine, tri-tert-butylphosphine,tricyclohexylphosphine, 2-(dicyclohexylphosphine)biphenyl,2-(di-tert-butylphosphine)biphenyl,2-(dicyclohexylphosphine)-2′-(N,N-dimethylamino)biphenyl,triphenylphosphine, tris-(o-tolyl)phosphine, sodium3-(diphenylphosphino)benzenesulfonate, tris-2-(methoxyphenyl)phosphine,2,2′-bis(diphenylphosphine)-1,1′-binaphthyl,1,4-bis(di-phenylphosphine)butane, 1,2-bis(diphenylphosphine)ethane,1,4-bis(dicyclohexylphosphine)-butane,1,2-bis(dicyclohexylphosphine)ethane,2-(dicyclohexylphosphine)-2′-(N,N-dimethylamino)biphenyl,bis(diphenylphosphino)ferrocene or tris-(2,4-tert-butylphenyl)-phosphiteto the reaction.

To carry out the process (b) according to the invention for preparingthe compounds of the formula (I), in general from 1 to 15 mol,preferably from 2 to 8 mol, of the boronic acid derivative of theformula (V) are employed per mole of the halooxathiincarboxamide of theformula (IV).

To carry out the process (c) according to the invention for preparingthe compounds of the formula (I), in general from 0.8 to 15 mol,preferably from 0.8 to 8 mol, of the phenyl derivative of the formula(VII) are employed per mole of the oxathiincarboxamideboronic acidderivative of the formula (VI).

To carry out the process (d) according to the invention for preparingthe compounds of the formula (I), in general from 0.8 to 15 mol,preferably from 0.8 to 8 mol, of the phenyl derivative of the formula(VII) and from 0.8 to 15 mol, preferably from 0.8 to 8 mol, of4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane are employedper mole of the halooxathiincarboxamide of the formula (IV).

Suitable diluents for carrying out the process (e) according to theinvention are all inert organic solvents. These preferably includealiphatic or alicyclic hydrocarbons, such as, for example, petroleumether, hexane, heptane, cyclohexane, methylcyclohexane or decalin;ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether,methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or1,2-diethoxyethane; alcohols, such as methanol, ethanol, n- ori-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol,ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether,diethylene glycol monoethyl ether, mixtures thereof with water or purewater.

The (e) process according to the invention is carried out in thepresence of a catalyst. Suitable catalysts are all those commonlyemployed for hydrogenations. Examples which may be mentioned are: Raneynickel, palladium and platinum, if appropriate on a support, such as,for example, activated carbon.

When carrying out the process (e) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures of from 0° C. to150° C., preferably at temperatures of from 20° C. to 100° C.

Suitable diluents for carrying out the process (f) according to theinvention are all inert organic solvents. These preferably includealiphatic, alicyclic or aromatic hydrocarbons, such as, for example,petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as,for example, chlorobenzene, dichlorobenzene, dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane;ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether,methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisole; ketones, such as acetone, butanone,methyl isobutyl ketone or cyclohexanone; nitriles, such as acetonitrile,propionitrile, n- or i-butyronitrile or benzonitrile; amides, such asN,N-dimethyl-formamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such asmethyl acetate or ethyl acetate; sulfoxides, such as dimethyl sulfoxide;sulfones, such as sulfolane; alcohols, such as methanol, ethanol, n- ori-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol,ethoxyethanol, methoxy-ethanol, diethylene glycol monomethyl ether,diethylene glycol monoethyl ether, mixtures thereof with water or purewater.

The process (f) according to the invention is, if appropriate, carriedout in the presence of an acid. Suitable acids are all inorganic andorganic protic and Lewis acids, and also all polymeric acids. Theseinclude, for example, hydrogen chloride, sulfuric acid, phosphoric acid,formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid,trifluoromethane-sulfonic acid, toluenesulfonic acid, boron trifluoride(also as etherate), boron tribromide, aluminum trichloride, titaniumtetrachloride, tetrabutyl orthotitanate, zinc chloride, iron(III)chloride, antimony pentachloride, acidic ion exchangers, acidic aluminasand acidic silica gels.

When carrying out the process (f) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures of from 0° C. to150° C., preferably at temperatures of from 0° C. to 100° C.

Suitable diluents for carrying out the process (g) according to theinvention are all inert organic solvents. These preferably includenitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile orbenzonitrile, or amides, such as N,N-dimethylformamide,N,N-dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide.

The process (g) according to the invention is, if appropriate, carriedout in the presence of a suitable acid acceptor. Suitable acid acceptorsare all customary inorganic or organic bases. These preferably includealkaline earth metal or alkali metal hydrides, hydroxides, amides,alkoxides, acetates, carbonates or bicarbonates, such as, for example,sodium hydride, sodium amide, sodium methoxide, sodium ethoxide,potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammoniumhydroxide, sodium acetate, potassium acetate, calcium acetate, ammoniumacetate, sodium carbonate, potassium carbonate, potassium bicarbonate,sodium bicarbonate or ammonium carbonate, and also tertiary amines, suchas trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzyl-amine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

The process (g) according to the invention is carried out in thepresence of one or more catalysts.

Suitable catalysts are in particular palladium salts or complexes. Theseare preferably palladium chloride, palladium acetate,tetrakis(triphenylphosphine)palladium orbis-(triphenylphosphine)palladium dichloride. It is also possible togenerate a palladium complex in the reaction mixture by adding apalladium salt and a complex ligand separately to the reaction.

Preferred ligands are organophosphorus compounds. Examples which may bementioned are: triphenylphosphine, tri-o-tolylphosphine,2,2′-bis(diphenylphosphino)-1,1′-binaphthyl,dicyclohexylphosphinebiphenyl, 1,4-bis(diphenylphosphino)butane,bisdiphenylphosphino-ferrocene, di-(tert-butylphosphino)biphenyl,di(cyclohexylphosphino)biphenyl,2-dicyclohexylphosphino-2′-N,N-dimethylaminobiphenyl,tricyclohexylphosphine, tri-tert-butylphosphine. However, ligands mayalso be dispensed with.

Furthermore, the process (g) according to the invention is, ifappropriate, carried out in the presence of a further metal salt, suchas a copper salt, for example copper(I) iodide.

When carrying out the process (g) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures of from 20° C. to180° C., preferably at temperatures of from 50° C. to 150° C.

For carrying out the process (g) according to the invention forpreparing the compounds of the formula (I), in general from 1 to 5 mol,preferably from 1 to 2 mol, of the alkyne of the formula (IX) or thealkene of the formula (X) are employed per mole of thehalooxathiincarboxamide of the formula (IV).

Suitable diluents for carrying out the process (h) according to theinvention are all inert organic solvents. These preferably includealiphatic, alicyclic or aromatic hydrocarbons, such as, for example,petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as,for example, chlorobenzene, dichlorobenzene, dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane;ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether,methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisole; nitriles, such as acetonitrile,propionitrile, n- or i-butyronitrile or benzonitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide,N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such asmethyl acetate or ethyl acetate; sulfoxides, such as dimethylsulfoxide;sulfones, such as sulfolane; alcohols, such as methanol, ethanol, n- ori-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol,ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether,diethylene glycol monoethyl ether.

The process (h) according to the invention is, if appropriate, carriedout in the presence of a suitable acid acceptor. Suitable acid acceptorsare all customary strong bases. These preferably include alkaline earthmetal or alkali metal hydrides, hydroxides, amides, alkoxides or alkalimetal hydrocarbon compounds, such as, for example, sodium hydride,sodium hydroxide, potassium hydroxide, sodium amide, lithiumdiisopropylamide, sodium methoxide, sodium ethoxide, potassiumtert-butoxide, methylithium, phenyllithium or butyllithium.

When carrying out the process (h) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures of from −80° C. to150° C., preferably at temperatures of from −30° C. to 80° C.

To carry out the process (h) according to the invention for preparingcompounds of the formula (I), in general from 1 to 5 mol, preferablyfrom 1 to 2 mol, of the phosphorus compound of the formula (XII) areemployed per mole of the ketone of the formula (XI).

Suitable diluents for carrying out the process (i) according to theinvention are all inert organic solvents. These preferably includealiphatic, alicyclic or aromatic hydrocarbons, such as, for example,petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as,for example, chlorobenzene, dichlorobenzene, dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane;ethers, such as diethyl ether, diisopropyl ether, methyl tert-butylether, methyl tert-amyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; or amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide.

The process (i) according to the invention is carried out in thepresence of a base. Suitable bases are all customary inorganic ororganic bases. These preferably include alkaline earth metal or alkalimetal hydrides, hydroxides, amides, alkoxides, acetates, carbonates orbicarbonates, such as, for example, sodium hydride, sodium amide, sodiummethoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide,potassium hydroxide, ammonium hydroxide, sodium acetate, potassiumacetate, calcium acetate, ammonium acetate, sodium carbonate, potassiumcarbonate, potassium bicarbonate, sodium bicarbonate or cesiumcarbonate, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methyl-piperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the process (i) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures of from 0° C. to150° C., preferably at temperatures of from 20° C. to 110° C.

To carry out the process (i) according to the invention for preparingthe compounds of the formula (I), in general from 0.2 to 5 mol,preferably from 0.5 to 2 mol, of the halide of the formula (XIII) areemployed per mole of the oxathiincarboxamide of the formula (Ib).

All processes according to the invention are generally carried out underatmospheric pressure. However, it is also possible to operate underelevated or reduced pressure—in general between 0.1 bar and 10 bar.

The compounds according to the invention have potent microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The active compounds according to the invention also have very goodfortifying action in plants. Accordingly, they can be used formobilizing the defenses of the plant against attack by undesirablemicroorganisms.

In the present context, plant-fortifying (resistance-inducing)substances are to be understood as meaning those substances which arecapable of stimulating the defense system of plants such that, when thetreated plants are subsequently inoculated with undesirablemicroorganisms, they show substantial resistance to thesemicroorganisms.

In the present case, undesirable microorganisms are to be understood asmeaning phytopathogenic fungi, bacteria and viruses. Accordingly, thesubstances according to the invention can be used to protect plants fora certain period after the treatment against attack by the pathogensmentioned. The period for which protection is provided generally extendsover 1 to 10 days, preferably 1 to 7 days, after the treatment of theplants with the active compounds.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds according to the invention can be used withparticularly good results for controlling cereal diseases, such as, forexample, against Pyrenophora species, diseases in viticulture and in thecultivation of fruit and vegetables, such as, for example, againstBotrytis, Venturia or Altemaria species.

The active compounds according to the invention are also suitable forincreasing the yield of crops. In addition, they show reduced toxicityand are well tolerated by plants.

At certain concentrations and application rates, the active compoundsaccording to the invention can also if appropriate be used asherbicides, for influencing plant growth and for controlling animalpests. If appropriate, they can also be used as intermediates andprecursors for the synthesis of further active compounds.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and inclusive of the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offshoots and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on the surroundings, environment or storage space bythe customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

In the protection of materials, the substances according to theinvention can be employed for protecting industrial materials againstinfection with, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnonliving materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular molds, wood-discoloring andwood-destroying fungi (Basidiomycetes), and against slime organisms andalgae.

Microorganisms of the following genera may be mentioned as examples:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, and

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Essentially,suitable liquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulfoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, corn cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulfonates, alkyl sulfates, arylsulfonates, or else proteinhydrolyzates. Suitable dispersants are: for example lignosulfite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such orin their formulations, also in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Examples of suitable mixing components are the following compounds:

Fungicides:

2-phenylphenol; 8-hydroxyquinoline sulfate; acibenzolar-5-methyl;aldimorph; amidoflumet; ampropylfos; ampropylfos-potassium; andoprim;anilazine; azaconazole; azoxystrobin; benalaxyl; benodanil; benomyl;benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos;binapacryl; biphenyl; bitertanol; blasticidin-S; bromuconazole;bupirimate; buthiobate; butylamine; calcium polysulfide; capsimycin;captafol; captan; carbendazim; carboxin; carpropamid; carvone;chinomethionat; chlobenthiazone; chlorfenazole; chloroneb;chlorothalonil; chlozolinate; clozylacon; cyazofamid; cyflufenamid;cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb;dichlofluanid; dichlone; dichlorophen; diclocymet; diclomezine;dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol;dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap;diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon;edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram;fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin;fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover;flumorph; fluoromide; fluoxastrobin; fluquinconazole; flurprimidol;flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl-Al;fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; furcarbanil;furmecyclox; guazatine; hexachlorobenzene; hexaconazole; hymexazole;imazalil; imibenconazole; iminoctadine triacetate; iminoctadinetris(albesil); iodocarb; ipconazole; iprobenfos; iprodione;iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin;kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil;metalaxyl; metalaxyl-M; metconazole; methasulfocarb; methfuroxam;metiram; metominostrobin; metsulfovax; mildiomycin; myclobutanil;myclozolin; natamycin; nicobifen; nitrothal-isopropyl; noviflumuron;nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole;oxycarboxin; oxyfenthiin; paclobutrazole; pefurazoate; penconazole;pencycuron; phosdiphen; phthalide; picoxystrobin; piperalin; polyoxins;polyoxorim; probenazole; prochloraz; procymidone; propamocarb;propanosine-sodium; propiconazole; propineb; proquinazid;prothioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil;pyroquilon; pyroxyfur; pyrrolenitrine; quinconazole; quinoxyfen;quintozene; simeconazole; spiroxamine; sulfur; tebuconazole;tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole;thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid;tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil;triazoxide; tricyclamide; tricyclazole; tridemorph; trifloxystrobin;triflumizole; triforine; triticonazole; uniconazole; validamycin A;vinclozolin; zineb; ziram; zoxamide;(2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanamide;1-(1-naphthalenyl)-1H-pyrrole-2,5-dione;2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine;2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide;2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide;3,4,5-trichloro-2,6-pyridinedicarbonitrile; actinovate;cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol; methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate;monopotassium carbonate;N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide;N-butyl-8-(1,1-dimethylethyl)-1-oxaspiro[4.5]decane-3-amine; sodiumtetrathiocarbonate; and copper salts and preparations, such as Bordeauxmixture; copper hydroxide; copper naphthenate; copper oxychloride;copper sulfate; cufraneb; cuprous oxide; mancopper; oxine-copper.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulfate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole,acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb;aldoxycarb, allethrin, allethrin 1R-isomers, alpha-cypermethrin(alphamethrin), amidoflumet, aminocarb, amitraz, avermectin, AZ-60541,azadirachtin, azamethiphos, azinphos-methyl, azinphos-ethyl,azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis,Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillusthuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821,baculoviruses, Beauveria bassiana, Beauveria tenella, bendiocarb,benfuracarb, bensultap, benzoximate, beta-cyfluthrin, beta-cypermethrin,bifenazate, bifenthrin, binapacryl, bioallethrin,bioallethrin-5-cyclopentyl-isomer, bioethanomethrin, biopermethrin,bioresmethrin, bistrifluron, BPMC, brofenprox, bromophos-ethyl,bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG-505, bufencarb,buprofezin, butathiofos, butocarboxim, butoxycarboxim, butylpyridaben,cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion,carbosulfan, cartap, CGA-50439, chinomethionat, chlordane,chlordimeform, chloethocarb, chlorethoxyfos, chlorfenapyr,chlorfenvinphos, chlorfluazuron, chlormephos, chlorobenzilate,chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos (-ethyl),chlovaporthrin, chromafenozide, cis-cypermethrin, cis-resmethrin,cis-permethrin, clocythrin, cloethocarb, clofentezine, clothianidin,clothiazoben, codlemone, coumaphos, cyanofenphos, cyanophos, cycloprene,cycloprothrin, Cydia pomonella, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyphenothrin (1R-trans-isomer), cyromazine, DDT,deltamethrin, demeton-5-methyl, demeton-5-methylsulfone, diafenthiuron,dialifos, diazinon, dichlofenthion, dichlorvos, dicofol, dicrotophos,dicyclanil, diflubenzuron, dimethoate, dimethylvinphos, dinobuton,dinocap, dinotefuran, diofenolan, disulfoton, docusat-sodium, dofenapyn,DOWCO-439, eflusilanate, emamectin, emamectin-benzoate, empenthrin(1R-isomer), endosulfan, Entomopthora spp., EPN, esfenvalerate,ethiofencarb, ethiprole, ethion, ethoprophos, etofenprox, etoxazole,etrimfos, famphur, fenamiphos, fenazaquin, fenbutatin oxide,fenfluthrin, fenitrothion, fenobucarb, fenothiocarb, fenoxacrim,fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate,fensulfothion, fenthion, fentrifanil, fenvalerate, fipronil, flonicamid,fluacrypyrim, fluazuron, flubenzimine, flubrocythrinate, flucycloxuron,flucythrinate, flufenerim, flufenoxuron, flufenprox, flumethrin,flupyrazofos, flutenzin (flufenzine), fluvalinate, fonofos, formetanate,formothion, fosmethilan, fosthiazate, fubfenprox (fluproxyfen),furathiocarb, gamma-HCH, gossyplure, grandlure, granulosis viruses,halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron,hexythiazox, hydramethylnone, hydroprene, IKA-2002, imidacloprid,imiprothrin, indoxacarb, iodofenphos, iprobenfos, isazofos, isofenphos,isoprocarb, isoxathion, ivermectin, japonilure, kadethrin, nuclearpolyhedrosis viruses, kinoprene, lambda-cyhalothrin, lindane, lufenuron,malathion, mecarbam, mesulfenfos, metaldehyde, metam-sodium,methacrifos, methamidophos, Metharhizium anisopliae, Metharhiziumflavoviride, methidathion, methiocarb, methomyl, methoprene,methoxychlor, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos, moxidectin,MTI-800, naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide,nicotine, nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250,NNI-9768, novaluron, noviflumuron, OK-5101, OK-5201, OK-9601, OK-9602,OK-9701, OK-9802, omethoate, oxamyl, oxydemeton-methyl, Paecilomycesfumosoroseus, parathion-methyl, parathion (-ethyl), permethrin (cis-,trans-), petroleum, PH-6045, phenothrin (1R-trans isomer), phenthoate,phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim,piperonyl butoxide, pirimicarb, pirimiphosmethyl, pirimiphosethyl,prallethrin, profenofos, promecarb, propaphos, propargite, propetamphos,propoxur, prothiofos, prothoate, protrifenbute, pymetrozine, pyraclofos,pyresmethrin, pyrethrum, pyridaben, pyridalyl, pyridaphenthion,pyridathion, pyrimidifen, pyriproxyfen, quinalphos, resmethrin, RH-5849,ribavirin, RU-12457, RU-15525, S-421, S-1833, salithion, sebufos,SI-0009, silafluofen, spinosad, spirodiclofen, spiromesifen,sulfluramid, sulfotep, sulprofos, SZI-121, tau-fluvalinate,tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin,temephos, temivinphos, terbam, terbufos, tetrachlorvinphos, tetradifon,tetramethrin, tetramethrin (1R-isomer), tetrasul, theta-cypermethrin,thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogenoxalate, thiodicarb, thiofanox, thiometon, thiosultap-sodium,thuringiensin, tolfenpyrad, tralocythrin, tralomethrin, transfluthrin,triarathene, triazamate, triazophos, triazuron, trichlophenidine,trichlorfon, triflumuron, trimethacarb, vamidothion, vaniliprole,verbutin, Verticillium lecanii, WL-108477, WL-40027, YI-5201, YI-5301,YI-5302, XMC, xylylcarb, ZA-3274, zeta-cypermethrin, zolaprofos,ZXI-8901, the compound 3-methylphenyl propylcarbamate (tsumacide Z), thecompound3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane-3-carbonitrile(CAS-Reg. No. 185982-80-3) and the corresponding 3-endo-isomer (CAS-Reg.No. 185984-60-5) (cf. WO-96/37494, WO-98/25923),

and also preparations which comprise insecticidally active plantextracts, nematodes, fungi or viruses.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, safeners or semiochemicals, is alsopossible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, molds and diphasic fungi (for example against Candida species,such as Candida albicans, Candida glabrata), and Epidermophytonfloccosum, Aspergillus species, such as Aspergillus niger andAspergillus fumigatus, Trichophyton species, such as Trichophytonmentagrophytes, Microsporon species such as Microsporon canis andaudouinii. The list of these fungi by no means limits the mycoticspectrum covered, but is only for illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low-volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10 000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10 000 g/ha, preferablybetween 1 and 5000 g/ha.

As already mentioned above, it is possible to treat all plants or theirparts in accordance with the invention. In a preferred embodiment, wildplant species or plant varieties and plant cultivars which have beenobtained by traditional biological breeding methods, such ashybridization or protoplast fusion, and the parts of these varieties andcultivars are treated. In a further preferred embodiment, transgenicplants and plant cultivars which have been obtained by recombinantmethods, if appropriate in combination with conventional methods(genetically modified organisms), and their parts are treated. The term“parts” or “parts of plants” or “plant parts” has been explained above.

Plants which are treated particularly preferably in accordance with theinvention are those of the plant cultivars which are in each casecommercially available or in use. Plant cultivars are understood asmeaning plants with new traits which have been bred either byconventional breeding, by mutagenesis or by recombinant DNA techniques.They may take the form of cultivars, biotypes and genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, nutrition), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widened activity spectrum and/or an increase in the activity ofthe substances and compositions which can be used in accordance with theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to salinity in the wateror soil, increased flowering performance, facilitated harvesting,accelerated maturation, higher yields, higher quality and/or betternutritional value of the harvested products, better storagecharacteristics and/or processability of the harvested products arepossible which exceed the effects which were actually to be expected.

The preferred transgenic plants or plant cultivars (those obtained byrecombinant methods) to be treated in accordance with the inventioninclude all those plants which, owing to the process of recombinantmodification, were given genetic material which confers particular,advantageous, valuable traits to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to salinity in the wateror soil, increased flowering performance, facilitated harvesting,accelerated maturation, higher yields, higher quality and/or highernutritional value of the harvested products, better storagecharacteristics and/or better processability of the harvested products.Further examples of such traits, examples which must be mentionedespecially, are better defense of the plants against animal andmicrobial pests, such as against insects, mites, phytopathogenic fungi,bacteria and/or viruses and an increased tolerance of the plants tocertain herbicidal active compounds. Examples of transgenic plants whichmay be mentioned are the important crop plants, such as cereals (wheat,rice), corn, soybeans, potatoes, cotton, tobacco, oilseed rape and fruitplants (with the fruits apples, pears, citrus fruits and grapes), withparticular emphasis on corn, soybeans, potatoes, cotton, tobacco, andoilseed rape. Traits which are especially emphasized are the increaseddefense of the plants against insects, arachnids, nematodes, and slugsand snails owing to toxins being formed in the plants, in particulartoxins which are generated in the plants by the genetic material ofBacillus thuringiensis (for example by the genes CryIA(a), CryIA(b),CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF andtheir combinations; hereinbelow “Bt plants”). Other traits which areparticularly emphasized are the increased defense of plants againstfungi, bacteria and viruses by the systemic acquired resistance (SAR),systemin, phytoalexins, elicitors and resistance genes andcorrespondingly expressed proteins and toxins. Other traits which areespecially emphasized are the increased tolerance of the plants tocertain herbicidal active compounds, for example imidazolinones,sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).The genes which confer the desired traits in each case may also bepresent in the transgenic plants in combination with one another.Examples of “Bt plants” which may be mentioned are corn cultivars,cotton cultivars, soybean cultivars and potato cultivars which arecommercially available under the trade names YIELD GARD® (for examplecorn, cotton, soybean), KnockOut® (for example corn), StarLink® (forexample corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare corn cultivars, cotton cultivars and soybean cultivars which arecommercially available under the trade names Roundup Ready® (toleranceto glyphosate, for example corn, cotton, soybean), Liberty Link®(tolerance to phosphinotricin, for example oilseed rape), IMI®(tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, forexample corn). Herbicide-resistant plants (plants bred in a conventionalmanner for herbicide tolerance) which may be mentioned include also thevarieties commercially available under the name Clearfield® (for examplecorn). Naturally, these statements also apply to plant cultivars havingthese genetic traits or genetic traits still to be developed, whichplant cultivars will be developed and/or marketed in the future.

The plants listed can be treated particularly advantageously accordingto the invention with the compounds of the general formula (I) or theactive compound mixtures according to the invention. The preferredranges stated above for the active compounds and mixtures also apply tothe treatment of these plants. Particular emphasis may be given to thetreatment of plants with the compounds or mixtures specificallymentioned in the present text.

The preparation and the use of the active compounds according to theinvention is illustrated in the examples below.

PREPARATION EXAMPLES Example 1

Process a)

A mixture of 6 ml of dichloromethane, 100 mg (0.467 mmol) of6-trifluoromethyl-2,3-di-hydro-1,4-oxathiin-5-carboxylic acid, 88 mg(0.389 mmol) of 2′-aminobiphenyl-4-carbaldehyde O-methyl oxime, 100.6 mg(0.778 mmol) of N,N-diisopropylethylamine and 272 mg (0.584 mmol) ofbromotripyrrolidinophosphonium hexafluorophosphate is stirred at roomtemperature for 2 days. 10 ml of water are then added to the reactionmixture and the organic phase is separated off and washed first with 10ml of saturated ammonium chloride solution and then with 10 ml of water,dried over sodium sulfate and evaporated. The crude product is purifiedby preparative HPLC (reversed-phase silica gel (C₁₈), mobile phase:water/acetonitrile 34:66).

This gives: 35 mg (21% of theory) ofN-[4′-(methoxyiminomethyl)-biphenyl-2-yl]-6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxamideof logP (pH 2.3)=3.51.

Example 2

Process a)

300 mg (1.7 mmol) of6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carbonyl chloride and 220mg (1.1 mmol) of 2-(1,3,3-trimethylbutyl)phenylamine in 5 ml ofacetonitrile are stirred in a closed vessel at room temperature for 4days. 10 ml of water are then added to the reaction mixture and theorganic phase is separated off and washed initially with 10 ml ofsaturated ammonium chloride solution and then with 10 ml of water, driedover sodium sulfate and evaporated. The crude product is purified bypreparative HPLC (reversed-phase silica gel (C₁₈), mobile phase: 2%strength acetic acid/acetonitrile 25:75).

This gives: 200 mg (37% of theory) ofN-[2-(1,3,3-trimethylbutyl)phenyl]-6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxamideof logP (pH 2.3)=4.18.

The compounds of the formula (I) listed in table 1 below were alsoobtained analogously to Examples 1 and 2 and in accordance with what wasstated in the general description of the preparation processes (a) to(h) according to the invention: TABLE 1 (I)

logP No. Z R⁴ R³ R² R¹ R⁵ n G² G³ G¹ m.p. 3 1,3-dimethylbutyl H H H H H0 H CH₃ CF₃ 4.24 4 1,3,3-trimethylbutyl H H H H H 0 H CH₃ CF₃ 4.53 54-fluoro-3-methylphenyl H H H H H 0 H CH₃ CF₃ 3.98 6 3,4-dichlorophenylH H H H H 0 H CH₃ CF₃ 4.26 7 4-chloro-3-trifluoro- H H H H H 0 H CH₃ CF₃4.30 methylphenyl 8 4-isopropoximinomethyl- H H H H H 0 H CH₃ CF₃ 4.57phenyl 9 4-trifluoromethylphenyl H H H H H 0 H CH₃ CF₃ 4.06 10cycloheptyl H H H H H 0 H H CF₃ 137° C. 11 cyclopentyl H H H H H 0 H HCF₃ 159° C. 12 —CH(CH₃)—CH₂—C(CH₃)₂— H H H H 0 H H CF₃ 165° C. 13cyclohexyl H F H H H 0 H H CF₃ 204-205° C. 14 cyclohexyl H Cl H H H 0 HH CF₃ 169-171° C. 15 bicyclo[2.2.1]hept-2-yl H H H H H 0 H H CF₃ 149° C.16 cyclooctyl H H H H H 0 H H CF₃ 102° C. 17 3,4-dichlorophenyl H F H HH 0 H H CF₃ 3.95 18 1,3-dimethylbutyl H H H H H 0 H H CF₃ 3.92 193,4-dichlorophenyl H H H H H 0 H H CF₃ 3.91 20 4-trifluoromethylphenyl HH H H H 0 H H CF₃ 3.73 21 4-isopropoximinomethyl-phenyl H H H H H 0 H HCF₃ 4.22 22 4-propoxyiminomethyl H H H H H 0 H H CF₃ 4.25 234-chloro-3-fluorophenyl H H H H H 0 H H CF₃ 3.62 243-chloro-4-fluorophenyl H H H H H 0 H H CF₃ 3.60 253-fluoro-4-propoxyimino-methylphenyl H H H H H 0 H H CF₃ 4.42 264-chloro-2-methylphenyl H H H H H 0 H H CF₃ 4.00 27 4-bromophenyl H H HH H 0 H H CF₃ 3.70 28 cyclohexyl H H H H H 0 H H CF₃ 3.69 293-fluoro-4-trifluoromethyl-phenyl H H H H H 0 H H CF₃ 3.75 114-116° C.30 4-chloro-3-trifluoro- H H H H H 0 H H CF₃ 4.03 methylphenyl 31(2-cyclohexyl)-1-methylethyl H H H H H 0 H H CF₃ 4.71 323,5-difluorophenyl H H H H H 0 H H CF₃ 3.35 167° C. 33 4-iodophenyl H HH H H 0 H H CF₃ 3.85 34 1-methyl-3-butenyl H H H H H 0 H H CF₃ 3.33 354-fluoro-3-methylphenyl H H H H H 0 H H CF₃ 3.65 363-fluoro-4-methylphenyl H H H H H 0 H H CF₃ 3.62 37(2-cyclopentyl)-1-methylethyl H H H H H 0 H H CF₃ 4.38 383-chloro-4-methylphenyl H H H H H 0 H H CF₃ 3.89 39 1-methylbutyl H H HH H 0 H H CF₃ 3.63 40 4-(1-(3-propynyloxy- H H H H H 0 H H CF₃ 3.76imino)ethyl)phenyl 125-127° C. 41 4-(1-amino-1-methoxy- H H H H H 0 H HCF₃ 1.96 iminomethyl)phenyl 42 1-methylnonyl H H H H H 0 H H CF₃ 5.48 434-bromo-2-fluorophenyl H H H H H 0 H H CF₃ 3.57 443-chloro-5-fluorophenyl H H H H H 0 H H CF₃ 3.60 453-chloro-4-(1-methoxy- H H H H H 0 H H CF₃ 3.45 iminoethyl)phenyl 463-fluoro-4-(1-methoxy- H H H H H 0 H H CF₃ 3.69 iminoethyl)phenyl 47bicyclo[2.2.1]hept-2-yl H H H H H 0 H H CF₃ 4.32 48 1-methylhexyl H H HH H 0 H H CF₃ 4.34 49 1-cyclohexylethyl H H H H H 0 H H CF₃ 4.31 501,3-dimethylbutyl H F H H H 0 H H CF₃ 3.94 51 1-ethylpropyl H H H H H 0H H CF₃ 3.62 52 1-methylbutyl H F H H H 0 H H CF₃ 3.67 533-chloro-4-trifluoro- H H H H H 0 H H CF₃ 3.98 methylphenyl 100-102° C.54 1,3-dimethylpentyl H H H H H 0 H H CF₃ 4.25 55 2-(2,2-dichlorocyclo-H H H H H 0 H H CF₃ 3.92 propyl)-1-methylethyl 56 4-(1-methoxyimino- H HH H H 0 H H CF₃ 4.08 propyl)phenyl 57 4-bromo-3-fluorophenyl H H H H H 0H H CF₃ 3.69 58 1,3,3-trimethylpentyl H H H H H 0 H H CF₃ 4.48 59bicyclo[2.2.1]hept-2-yl H H H H H 0 CH₃ H CF₃ 5.36 60—CH(CH₃)—CH₂—C(CH₃)₂— H H H H 0 H H CF₃ 4.18 61 4-trifluoromethylphenylH H H H H 0 CH₃ H CF₃ 4.08 62 4-methoxyiminomethyl- H H H H H 0 CH₃ HCF₃ 3.81 phenyl 63 1,3-dimethylbutyl H H H H H 0 CH₃ H CF₃ 4.27 644-isopropoximinomethyl- H H H H H 0 CH₃ H CF₃ 4.56 phenyl 653,4-dichlorophenyl H H H H H 0 CH₃ H CF₃ 4.27 66 1,3,3-trimethylbutyl HH H H H 0 CH₃ H CF₃ 4.51 67 3,4-dichlorophenyl H F H H H 0 CH₃ H CF₃4.32 68 3-fluoro-4-propoxyimino- H H H H H 0 CH₃ H CF₃ 4.77 methylphenyl69 3-fluoro-4-methylphenyl H H H H H 0 CH₃ H CF₃ 3.99 704-fluoro-3-methylphenyl H H H H H 0 CH₃ H CF₃ 3.99 713-fluoro-4-trifluoromethyl- H H H H H 0 CH₃ H CF₃ 4.08 phenyl 722-chloro-4-methoxyiminophenyl H H H H H 0 H H CF₃ 3.81 733,5-difluorophenyl H F H H H 0 H H CF₃ 3.49 74 3,5-difluorophenyl H H HF H 0 H H CF₃ 3.20 75 3,5-difluorophenyl H H F H H 0 H H CF₃ 3.70 76n-hexyl H H H H H 0 H H CF₃ 4.25 77 1-ethylbutyl H H H H H 0 H H CF₃4.07 78 4-cyanophenyl H H H H H 0 H H CF₃ 2.87 79 2,4-dichlorophenyl H HH H H 0 H H CF₃ 3.82 80 3,4-dichlorophenyl H H H H H 0 H H cyclo- 3.53propyl 81 1,3,3-trimethylbutyl H H H H H 0 H H CHF₂ 4.29 821,3-dimethylbutyl H H H H H 0 H H CHF₂ 4.03 83 —CH(CH₃)—CH₂—C(CH₃)₂— H HH H 0 H H CHF₂ 4.00 84 3,4-dichlorophenyl H H H H H 0 H H CHF₂ 3.92 853-fluoro-4-propoxyimino- H H H H H 0 H H CHF₂ 4.52 methylphenyl 864-methoxyiminomethyl- H H H H H 0 H H CHF₂ phenyl 873-methyl-1-propylbutyl H H H H H 0 H H CF₃ 4.65 88 3-methyl-1-ethylbutylH H H H H 0 H H CF₃ 4.30 89 1,3-dimethyl-1-butenyl H H H H H 0 H H CF₃4.32 90 1,3-dimethylbutyl H H H H H 2 H H CF₃ 3.53 91 4-bromophenyl H HH H H 2 H H CF₃ 3.35 92 4-chloro-2-methylphenyl H H H H H 2 H H CF₃ 3.6693 3,4-dichlorophenyl H H H H H 2 H H CF₃ 3.57 94 1,2-dimethylbutyl H HH H H 0 H H CF₃ 3.88 95 4-chloro-3-fluorophenyl H H H H H 2 H H CF₃ 3.2896 (2-cyclopropyl)-1-methylethyl H H H H H 0 H H CF₃ 3.72 973,3-dimethyl-1-butynyl H H H H H 0 H H CF₃ 4.42 984-bromo-3-methylphenyl H H H H H 0 H H CF₃ 4.06 99 1,3-dimethylbutyl H HH H —COCH₃ 0 H H CF₃ 4.56 100 4-(2,2,2-trifluoro-N-meth- H H H H H 0 H HCF₃ 2.53 oxyethaneimidoyl)phenyl 101 2,2-dichloro-1-methyl-cyclopropyl HH H H H 0 H H CF₃ 3.66 102 3-methylbutyl H H H H H 0 H H CF₃ 3.72 1033,3-dimethylbutyl H H H H H 0 H H CF₃ 3.98Preparation of the Precursors of the Formula (II)

Example (II-1)

First step (II-1a):

At about 5° C., 10.17 g (0.09 mol) of triethylamine are added dropwiseto a solution of 20.0 g (0.092 mol) of ethyl2-chloro-3-keto-4,4,4-trifluorobutyrate in 100 ml of toluene. A solutionof 7.0 g (0.09 mol) of 2-mercaptoethanol in 5 ml of toluene is thenadded dropwise over a period of 1 hour, and the mixture is stirred atabout 5° C. for another 2 hours. The suspension is filtered off, and thefilter cake is washed with a little toluene. The filtrate is washedinitially with 50 ml of 1N hydrochloric acid, then twice with 50 ml ofsaturated sodium bicarbonate solution and finally with 50 ml of water,dried over magnesium sulfate and concentrated. This gives: 18.8 g (62%of theory) of ethyl4,4,4-trifluoro-2-(2-hydroxyethylsulfanyl)-3-oxobutyrate (cf.Heterocycles, 1998, 48, 2253-2262).Second Step (II-1b)

6.25 g (0.079 mol) of pyridine and then, dropwise over a period of 30minutes and at 20° C., 4 g (0.079 mol) of thionyl chloride are added toa solution of 18.7 g (0.071 mol) of ethyl4,4,4-trifluoro-2-(2-hydroxyethylsulfanyl)-3-oxobutyrate (II-1a) in 60ml of toluene. Owing to the exothermic reaction, the temperature of thereaction mixture has to be cooled with ice-water. After the vigorousreaction has ended, the mixture is stirred at room temperature foranother 5 hours. The mixture is filtered and the residue is washed with10 ml of toluene. At about 10° C., 10.9 g (0.108 mol) of triethylamineare added dropwise over a period of 1 hour to the filtrate, and themixture is stirred at room temperature for 16 hours. The reactionmixture is washed initially twice with 50 ml of 1N hydrochloric acid,then twice with 50 ml of saturated sodium bicarbonate solution andfinally with 50 ml of water, dried over magnesium sulfate andconcentrated. The residue is chromatographed on silica gel usingpetroleum ether/ethyl acetate (10:1 to 1:1).

This gives 12.6 g (59.4% of theory) of ethyl6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxylate (cf.Heterocycles 1998, 48, 2253-2262).Third Step:

12.6 g (0.05 mol) of ethyl6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxylate (II-1b) and3.14 g (0.08 mol) of sodium hydroxide in 50 ml of water are boiled underreflux for 1 hour. The reaction mixture is cooled and extracted twicewith dichloromethane. The aqueous phase is acidified to pH 2 using 6Nhydrochloric acid and then extracted 5 times with diethyl ether. Thecombined organic extracts are dried over sodium sulfate andconcentrated.

This gives: 9.2 g (82% of theory) of6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxylic acid.

The compounds of the formula (II) mentioned below were also obtainedanalogously to Example (II-1):

Example (II-2)

HPLC: logP=1.69

This compound is novel and also forms part of the subject-matter of thepresent application.

Example (II-3)

HPLC: logP=1.72

This compound is novel and also forms part of the subject-matter of thepresent application.

Example (II-4)

This compound is novel and also forms part of the subject-matter of thepresent application.

Example (II-5)

4.5 g (21 mmol) of6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxylic acid (II-1) and21 g of thionyl chloride in 10 ml of toluene are stirred at 80° C. for 4hours. The end of the reaction is determined by regularly taking samplesfrom the reaction solution, which samples are then mixed with methanoland used to prepare thin-layer chromatograms. After the reaction hasended, volatile components are distilled off. Three times, the residueis stirred with in each case 20 ml of dichloromethane andre-concentrated.

This gives 4.5 g (80% of theory) of6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carbonyl chloride. Theproduct was characterized by boiling a sample thereof with methanol for2 hours and detecting the methyl6-trifluoromethyl-2,3-dihydro-1,4-oxathiin-5-carboxylate obtained inthis manner by GC/MS.

Preparation of the Precursors of the Formula (III)

Example (III-1)

First Step III-1a)

At 0° C., the 15 g (124 mmol) of pivaloyl chloride are added dropwise toa solution of 15 g (124 mmol) of 2-ethylaniline and 25 g (248 mmol) oftriethylamine in 150 ml of dichloromethane, and the mixture is thenstirred at 0° C. for 2 hours and subsequently without further coolingfor 16 hours. The mixture is diluted with dichloromethane and washedinitially with water and then with ammonium chloride solution, and theorganic phase is separated off, dried over sodium sulfate andconcentrated.

This gives 25 g (98% of theory) ofN-(2-ethylphenyl)-2,2-dimethylpropionamide.Second Step (III-1b)

Under argon and at −25° C., initially 3.7 g (0.03 mol) ofdiazabicyclo[2.2.2]octane (DABCO) and then 44.5 ml (0.058 mol) of asolution of sec-butyllithium (1.3 M in hexane) are added to a solutionof 5.6 g (0.0275 mol) of N-(2-ethylphenyl)-2,2-dimethylpropionamide(III-1a) in 150 ml of n-pentane/methyl t-butyl ether (1:1), and themixture is then stirred at the same temperature for a further 2 hours.The mixture is then cooled to −78° C., 3.33 g (0.0275 mol) of allylbromide are added dropwise and the mixture is stirred at −60 to −78° C.for 60 minutes. Residual sec-butyllithium is destroyed by addition of 30ml of methanol. The mixture is warmed to room temperature and shakenwith 50 ml of 5% strength phosphoric acid. The organic phase isseparated off, filtered through silica gel and purified by preparativeHPLC (reversed-phase silica gel (C₁₈), mobile phase: water/acetonitrile38:62).

This gives 1.8 g (26% of theory) of2,2-dimethyl-N-[2-(1-methylbut-3-enyl)phenyl]-propionamide.Third Step (III-1)

1.5 g (6.1 mmol) of2,2-dimethyl-N-[2-(1-methylbut-3-enyl)phenyl]propionamide (III-1b) and1.2 g (12.2 mmol) of concentrated hydrochloric acid in 24.5 ml ofdioxane are stirred at 80° C. for 12 hours. 10 ml of water are added tothe reaction mixture, which is then made alkaline with dilute aqueoussodium hydroxide solution and extracted 5 times with ethyl acetate. Thecombined organic extracts are dried over sodium sulfate andconcentrated, filtered through silica gel (ethyl acetate/methanol 5:1)and purified by preparative HPLC (reversed-phase silica gel (C₁₈),mobile phase: 2% strength acetic acid/acetonitrile 70:30).

This gives 0.3 g (30% of theory) of 2-(1-methylbut-3-enyl)phenylamine.

The compounds of the formula (III) mentioned below were also obtainedanalogously to Example (III-1):

Example (III-2)

HPLC: logP=1.19

This compound is novel and also forms part of the subject-matter of thepresent application.

Example (III-3)

HPLC: logP=2.3

2-(3-Chloro-1-methylpentyl)phenylamine (III-3) is obtained by initiallypreparing N-[2-(2-cyclopropylisopropyl)phenyl]-2,2-dimethylpropanamideanalogously to Examples (III-1a) and (III-1b). In the third step, thematerial is reacted with hydrochloric acid which gives, in addition to2-(2-cyclopropylisopropyl)phenylamine, also the compound (III-3).

Example (III-4)

First Step (III-4a)

At room temperature, 100 mg of benzyltriethylammonium chloride and 1 mlof 50% strength aqueous sodium hydroxide solution are added successivelyto a solution of 900 mg (3.7 mmol) of2,2-dimethyl-N-[2-(1-methylbut-3-enyl)phenyl]propionamide (III-1b) in 5ml of chloroform/water (1:1), and the mixture is stirred for 5 days. Thereaction mixture is diluted further with 20 ml of chloroform and washedwith 50 ml of sodium chloride solution, and the organic phase isseparated off, dried over sodium sulfate and concentrated.

This gives 800 mg (37% of theory) ofN-{2-[2-(2,2-dichlorocyclopropyl)-1-methylethyl]-phenyl}-2,2-dimethylpropionamideof logP (pH 2.3)=3.77.

This compound is novel and also forms part of the subject-matter of thepresent invention.Second Step (III-4b)

800 mg (1.34 mmol) ofN-{2-[2-(2,2-dichlorocyclopropyl)-1-methylethyl]phenyl}-2,2-dimethylpropionamide(III-4a) are dissolved in 25 ml of dioxane, 0.1 ml of concentratedhydrochloric acid is added and the mixture is stirred at roomtemperature for 72 hours and at 80° C. for 24 hours. The mixture isdiluted with ice-water, made alkaline with concentrated aqueous sodiumhydroxide solution and extracted with 50 ml of ethyl acetate. Theorganic phase is dried over sodium sulfate and concentrated underreduced pressure. Using methanol, the residue is filtered through silicagel and purified by preparative HPLC (reversed-phase silica gel (C₁₈),mobile phase: 2% strength phosphoric acid/acetonitrile 52:48).

This gives 0.8 g (60% of theory) of2-[2-(2,2-dichlorocyclopropyl)-1-methylethyl]-phenylamine of logP (pH2.3)=2.52.

This compound is novel and also forms part of the subject-matter of thepresent application.

The given logP values were determined in accordance with EEC Directive79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on areversed-phase column (C 18). Temperature: 43° C.

Mobile phases for the determination in the acidic range (pH 2.3): 0.1%aqueous phosphoric acid, acetonitrile; linear gradient from 10%acetonitrile to 90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

USE EXAMPLES Example A

Venturia Test (Apple)/Protective

Solvents:

-   -   24.5 parts by weight of acetone    -   24.5 parts by weight of dimethylacetamide        Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the apple scab pathogen Venturia inaequalis andthen remain in an incubation cabin at about 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below. TABLE A Venturia test (apple)/protective Application rateof active Active compound in % Ex. compound g/ha efficacy 12

100 100 17

100 100 20

100 88 18

100 100 19

100 100 21

100 100 22

100 100 2

100 98

Example B

Botrytis Test (Bean)/Protective

Solvents:

-   -   24.5 parts by weight of acetone    -   24.5 parts by weight of dimethylacetamide        Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, 2 small pieces of agar colonized withBotrytis cinerea are placed onto each leaf. The inoculated plants areplaced in a dark chamber at about 20° C. and 100% relative atmospherichumidity.

2 days after the inoculation, the size of the infected areas on theleaves is evaluated. 0% means an efficacy which corresponds to that ofthe control, whereas an efficacy of 100% means that no infection isobserved.

Active compounds, application rates and test results are shown in thetable below. TABLE B Botrytis test (bean)/protective Application rate ofactive Active compound in % Ex. compound g/ha efficacy 12

500 97 17

500 96 20

500 100 18

500 100 19

500 100 21

500 100 22

500 100 2

500 100

Example C

Alternaria Test (Tomato)/Protective

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young tomato plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with a spore suspensionof Alternaria solani and are then allowed to stand at 100% relativehumidity and 20° C. for 24 h. The plants are then allowed to stand at96% relative atmospheric humidity and a temperature of 20° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below. TABLE C Alternaria test (tomato)/protective Applicationrate of active compound in % Ex. Active compound g/ha efficacy 26

750 100 2

750 100 19

750 100 21

750 100

Example D

Puccinia Test (Wheat)/Protective

Solvent: N,N-dimethylacetamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Puccinia recondite. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 h.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of 80% to promote the developmentof rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates, amounts of solvent, amounts ofemulsifier and test results are shown in the table below. TABLE DPuccinia test (wheat)/protective Application rate of active Parts byweight of solvent/ Ex. Active compound compound in g/ha % efficacyemulsifier 18

500 100 25/0.5 17

500 86 25/0.6 35

500 88 25/0.6 19

500 100 25/0.6 2

500 100 25/0.6 24

500 100 25/0.6 38

500 88 25/0.6 37

500 93 25/0.6 36

500 100 25/0.6 56

500 88 25/0.6 57

500 88 25/0.6 54

500 100 50/1.0 29

500 94 50/1.0 53

500 100 50/1.0 79

500 86 50/1.0 23

500 89 50/1.0 27

500 88 50/1.0 82

500 100 50/1.0

1-18. (canceled)
 19. An oxathiincarboxamide of formula (I)

in which G¹ represents halogen, trifluoro methyl, difluoromethyl, orcyclopropyl, G² and G³ independently of one another represent hydrogenor methyl, n represents 0, 1 or 2, R¹, R², R³, and R⁴ independently ofone another represent hydrogen, fluorine, chlorine, methyl, isopropyl,or methylthio, R⁵ represents hydrogen, C₁-C₈-alkyl, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl;represents C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl,halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl having in eachcase 1 to 9 fluorine, chlorine, and/or bromine atoms; representsformyl-C₁-C₃-alkyl, (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl, or(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl; represents(C₁-C₃-haloalkyl)carbonyl-C₁-C₃-alkyl or(C₁-C₃-haloalkoxy)-carbonyl-C₁-C₃-alkyl having in each case 1 to 7fluorine, chlorine, and/or bromine atoms; represents(C₁-C₃-alkyl)carbonyl-C₁-C₃-haloalkyl or(C₁-C₃-alkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 6fluorine, chlorine, and/or bromine atoms; represents(C₁-C₃-haloalkyl)carbonyl-C₁-C₃-haloalkyl or(C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 13fluorine, chlorine, and/or bromine atoms; or represents —COR⁶, —CONR⁷R⁸,or —CH₂NR⁹R¹⁰, R⁶ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl; representsC₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, orC₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine,and/or bromine atoms; or represents —COR¹¹, R⁷ and R⁸ independently ofone another represent hydrogen, C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,or C₃-C₈-cycloalkyl; represent C₁-C₈-haloalkyl,halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl having in eachcase 1 to 9 fluorine, chlorine, and/or bromine atoms; or R⁷ and R⁸together with the nitrogen atom to which they are attached form asaturated heterocycle having 5 to 8 ring atoms, where the heterocycleoptionally contains 1 or 2 further nonadjacent heteroatoms selected fromthe group consisting of oxygen, sulphur, and NR¹² and is optionallymono- or polysubstituted by identical or different substituents selectedfrom the group consisting of halogen and C₁-C₄-alkyl, R⁹ and R¹⁰independently of one another represent hydrogen, C₁-C₈-alkyl, orC₃-C₈-cycloalkyl; or represent C₁-C₈-haloalkyl, C₃-C₈-halocycloalkylhaving in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; orR⁹ and R¹⁰ together with the nitrogen atom to which they are attachedform a saturated hetero-cycle having 5 to 8 ring atoms, where theheterocycle optionally contains 1 or 2 further nonadjacent heteroatomsselected from the group consisting of oxygen, sulphur, and NR¹² and isoptionally mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of halogen andC₁-C₄-alkyl, R¹¹ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl; representsC₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, orC₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine,and/or bromine atoms, R¹² represents hydrogen or C₁-C₆-alkyl, and Zrepresents Z¹, Z², Z³, or Z⁴, where Z¹ represents phenyl that isoptionally mono- to pentasubstituted by identical or differentsubstituents, Z² represents cycloalkyl or bicycloalkyl that isoptionally mono- or poly-substituted by identical or differentsubstituents, Z³ represents unsubstituted C₂-C₂₀-alkyl or representsC₁-C₂₀-alkyl that is mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of halogen andC₃-C₆-cycloalkyl in which the cycloalkyl moiety is optionally mono- orpolysubstituted by identical or different substituents selected from thegroup consisting of halogen and C₁-C₄-alkyl, and Z⁴ representsC₂-C₂₀-alkenyl or C₂-C₂₀-alkynyl that are optionally mono- orpolysubstituted by identical or different substituents selected from thegroup consisting of halogen and C₃-C₆-cycloalkyl, where the cycloalkylmoiety is optionally be mono- or polysubstituted by identical ordifferent substituents selected from the group consisting of halogen andC₁-C₄-alkyl, or Z and R⁴ together with the carbon atoms to which theyare attached form an optionally substituted 5- or 6-membered carbocyclicor heterocyclic ring and R¹, R², and R³ independently of one anotherrepresent hydrogen or fluorine.
 20. The oxathiincarboxamide of formula(I) as claimed in claim 19 in which G¹ represents fluorine, chlorine,bromine, iodine, trifluoromethyl, difluoromethyl, or cyclopropyl, G² andG³ independently of one another represent hydrogen, or methyl, and nrepresents 0 or
 2. 21. The oxathiincarboxamide of formula (I) as claimedin claim 19 in which R⁵ represents hydrogen.
 22. The oxathiincarboxamideof formula (I) as claimed in claim 19 in which R¹ represents hydrogen,fluorine, chlorine, or methyl, R² represents hydrogen, fluorine,chlorine, isopropyl, or methylthio, R³ represents hydrogen, fluorine,chlorine, or methyl, and R⁴ represents hydrogen, fluorine, chlorine, ormethyl.
 23. The oxathiincarboxamide of formula (I) as claimed in claim19 in which Z represents Z¹, wherein Z¹ represents phenyl that isoptionally mono- to pentasubstituted by identical or differentsubstituents W¹, W¹ represents halogen, cyano, nitro, amino, hydroxyl,formyl, carboxyl, carbamoyl, or thiocarbamoyl; represents straight-chainor branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl,alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl, oralkylsulfonyl having in each case 1 to 8 carbon atoms; representsstraight-chain or branched alkenyl or alkenyloxy having in each case 2to 6 carbon atoms; represents -chain or branched haloalkyl, haloalkoxy,haloalkylthio, haloalkylsulfinyl, or haloalkylsulfonyl having in eachcase 1 to 6 carbon atoms and 1 to 13 identical or different halogenatoms; represents straight-chain or branched haloalkenyl orhaloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11identical or different halogen atoms; represents straight-chain orbranched alkylamino, dialkylamino, alkyl-carbonyl, alkylcarbonyloxy,alkoxycarbonyl, alkylaminocarbonyl, dialkyl-aminocarbonyl,arylalkylaminocarbonyl, or dialkylaminocarbonyloxy having 1 to 6 carbonatoms in the respective hydrocarbon chains; represents alkenylcarbonylor alkynylcarbonyl having 2 to 6 carbon atoms in the respectivehydrocarbon chains; represents cycloalkyl or cycloalkyloxy having ineach case 3 to 6 carbon atoms; represents doubly attached alkylenehaving 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms, ordioxy-alkylene having 1 or 2 carbon atoms, each of which radicals isoptionally mono- to tetrasubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,oxo, methyl, trifluoromethyl, and ethyl; represents a group

 in which Q¹ represents hydrogen, hydroxyl, alkyl having 1 to 4 carbonatoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine,chlorine, and/or bromine atoms, or cycloalkyl having 1 to 6 carbonatoms, and Q² represents hydroxyl, amino, methylamino, phenyl, orbenzyl; represents optionally cyano-, hydroxyl-, alkoxy-, alkylthio-,alkylamino-, dialkylamino-, or phenyl-substituted alkyl or alkoxy having1 to 4 carbon atoms; or represents alkenyloxy or alkynyloxy having ineach case 2 to 4 carbon atoms;  or  represents phenyl, phenoxy,phenylthio, benzoyl, benzoylethenyl, cinnamoyl, or heterocyclyl orphenylalkyl, phenylalkyloxy, phenylalkylthio, or heterocyclylalkylhaving in each case 1 to 3 carbon atoms in the respective alkylmoieties, each of which radicals is optionally mono- to trisubstitutedin the cyclic part by halogen and/or straight-chain or branched alkyl oralkoxy having 1 to 4 carbon atoms.
 24. The oxathiincarboxamide offormula (I) as claimed in claim 19 in which Z represents Z², wherein Z²represents cycloalkyl or bicycloalkyl having in each case 3 to 10 carbonatoms, each of which radicals is optionally mono- to tetrasubstituted byidentical or different substituents selected from the group consistingof halogen and/or C₁-C₄-alkyl.
 25. The oxathiincarboxamide of formula(I) as claimed in claim 19 in which Z represents Z³, wherein Z³represents unsubstituted C₂-C₂₀-alkyl or represents C₁-C₂₀-alkyl whichis monosubstituted or polysubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, iodine and C₃-C₆-cycloalkyl in which the cycloalkyl moiety isoptionally mono- to tetrasubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, iodine, C₁-C₄-alkyl, and C₁-C₄-haloalkyl.
 26. Theoxathiincarboxamide of formula (I) as claimed in claim 19 in which Zrepresents Z⁴, wherein Z⁴ represents C₂-C₂₀-alkenyl or C₂-C₂₀-alkynyl,each of which is mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, iodine, and C₃-C₆-cycloalkyl in which the cycloalkyl moiety isoptionally-mono- to tetrasubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, iodine, C₁-C₄-alkyl, and C₁-C₄-haloalkyl.
 27. A process forpreparing a oxathiincarboxamide of formula (I) as claimed in claim 19comprising (a) reacting an oxathiincarboxylic acid derivative of formula(II)

in which G¹, G², G³ and n are as defined for formula (I) in claim 19, X¹represents halogen or hydroxyl,  with an aniline derivative of formula(III)

in which R¹, R², R³, R⁴, R⁵, and Z are as defined for formula (I) inclaim 19,  optionally in the presence of a catalyst, optionally in thepresence of a condensing agent, optionally in the presence of an acidbinder, and optionally in the presence of a diluent, or (b) reacting ahalooxathiincarboxamide of formula (IV)

in which G¹, G², G³, n, R¹, R², R³, R⁴, and R⁵ are as defined forformula (I) in claim 19, and X² represents bromine or iodine,  with aboronic acid derivative of formula (V)

in which Z¹ is as defined for formula (I) in claim 19, and A¹ and A²each represent hydrogen or together represent tetramethyl-ethylene,  inthe presence of a catalyst, optionally in the presence of an acidbinder, and optionally in the presence of a diluent, or (c) reacting anoxathiincarboxamide boronic acid derivative of formula (VI)

in which G¹, G², G³, n, R¹, R², R³, R⁴, and R⁵ are as defined forformula (I) in claim 19, and A³ and A⁴ each represent hydrogen ortogether represent tetramethyl-ethylene,  with a phenyl derivative offormula (VII)X³-Z¹  (VII) in which Z¹ is as defined for formula (I) in claim 19, andX³ represents chlorine, bromine, iodine, or trifluoromethylsulfonate, in the presence of a catalyst, optionally in the presence of an acidbinder, and optionally in the presence of a diluent, or (d) reacting ahalooxathiincarboxamide of formula (IV)

in which G¹, G², G³, n, R¹, R², R³, R⁴, and R⁵ are as defined forformula (I) in claim 19, and X² represents bromine or iodine,  with aphenyl derivative of formula (VII)X³-Z¹  (VII) in which Z¹ is as defined for formula (I) in claim 19, andX³ represents chlorine, bromine, iodine, or trifluoromethylsulfonate, in the presence of a palladium or nickel catalyst and in the presenceof 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane,optionally in the presence of an acid binder, and optionally in thepresence of a diluent, or (e) hydrogenating an oxathiincarboxamide offormula (Ia)

in which G¹, G², G³, n, R¹, R², R³, R⁴, and R⁵ are as defined forformula (I) in claim 19, and X⁴ represents C₂-C₂₀-alkenyl orC₂-C₂₀-alkynyl, each of which is optionally mono- or polysubstituted byidentical or different substituents selected from the group consistingof halogen and C₃-C₆-cycloalkyl, where the cycloalkyl moiety for itspart may optionally be substituted by halogen and/or C₁-C₄-alkyl, optionally in the presence of a diluent and optionally in the presenceof a catalyst, or (f) dehydrating a hydroxyalkyloxathiincarboxamide offormula (VIII)

in which G¹, G², G³, n, R¹, R², R³, R⁴, and R⁵ are as defined forformula (I) in claim 19, and X⁵ represents C₂-C₂₀-hydroxyalkyl that isoptionally additionally mono- or polysubstituted by identical ordifferent substituents selected from the group consisting of halogen andC₃-C₆-cycloalkyl in which the cycloalkyl moiety is optionallysubstituted by halogen and/or C₁-C₄-alkyl,  optionally in the presenceof a diluent and optionally in the presence of an acid, or (g) reactinga halooxathiincarboxamide of formula (IV)

in which G¹, G², G³, n, R¹, R², R³, R⁴, and R⁵ are as defined forformula (I) in claim 19, and X² represents bromine or iodine,  with analkyne of formula (IX)HC

A⁵  (IX), in which A⁵ represents C₂-C₁₈-alkyl, each of which isoptionally mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of halogen andC₃-C₆-cycloalkyl in which the cycloalkyl moiety is optionallysubstituted by halogen and/or C₁-C₄-alkyl,  or with an alkene of theformula (X)

in which A⁶, A⁷ and A⁸ independently of one another each representhydrogen or alkyl that is optionally mono- or polysubstituted byidentical or different substituents selected from the group consistingof halogen and C₃-C₆-cycloalkyl in which the cycloalkyl moiety isoptionally substituted by halogen and/or C₁-C₄-alkyl and in which thetotal number of carbon atoms of the open-chain part of the molecule doesnot exceed the number 20,  optionally in the presence of a diluent,optionally in the presence of an acid binder, and in the presence of oneor more catalysts, or (h) reacting a ketone of formula (XI)

in which G¹, G², G³, n, R¹, R², R³, R⁴, and R⁵ are as defined forformula (I) in claim 19, and A⁹ represents hydrogen or C₁-C₁₈-alkyl thatis optionally mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of halogen andC₃-C₆-cycloalkyl in which the cycloalkyl moiety is optionallysubstituted by halogen and/or C₁-C₄-alkyl,  with a phosphorus compoundof formula (XII)A¹⁰-Px  (XII), in which A¹⁰ represents C₁-C₁₈-alkyl that is optionallymono- or polysubstituted by identical or different substituents selectedfrom the group consisting of halogen and C₃-C₆-cycloalkyl in which thecycloalkyl moiety is optionally substituted by halogen and/orC₁-C₄-alkyl, and Px represents a grouping —P⁺(C₆H₅)₃Cl⁻, —P⁺(C₆H₅)₃Br⁻,—P⁺(C₆H₅)₃I⁻, —P(═O)(OCH₃)₃, or —P(═O)(OC₂H₅)₃,  optionally in thepresence of a diluent, or (i) reacting an oxathiincarboxamide of formula(Ib)

in which G¹, G², G³, n, R¹, R², R³, R⁴, and Z are as defined for formula(I) in claim 19,  with a halide of formula (XIII)R⁵⁻¹—X⁶  (XIII) in which R⁵⁻¹ represents C₁-C₈-alkyl,C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, orC₃-C₈-cycloalkyl; represents C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl,halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl having in eachcase 1 to 9 fluorine, chlorine, and/or bromine atoms; representsformyl-C₁-C₃-alkyl, (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl, or(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl; represents(C₁-C₃-haloalkyl)carbonyl-C₁-C₃-alkyl or(C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 7fluorine, chlorine, and/or bromine atoms; represents(C₁-C₃-alkyl)carbonyl-C₁-C₃-haloalkyl or(C₁-C₃-alkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 6fluorine, chlorine, and/or bromine atoms; represents(C₁-C₃-haloalkyl)carbonyl-C₁-C₃-haloalkyl or(C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 13fluorine, chlorine, and/or bromine atoms; or represents —COR⁶, —CONR⁷R⁸or —CH₂NR⁹R¹⁰ in which R⁶, R⁷, R⁸, R⁹ and R¹⁰ are as defined for formula(I) in claim 19, and X⁶ represents chlorine, bromine or iodine,  in thepresence of a base and in the presence of a diluent.
 28. A compositionfor controlling unwanted microorganisms comprising one or moreoxathiincarboxamides of formula (I) as claimed in claim 19 and one ormore extenders and/or surfactants.
 29. A method for controlling unwantedmicroorganisms comprising applying one or more oxathiincarboxamides offormula (I) as claimed in claim 19 to the microorganisms and/or theirhabitat.
 30. A process for preparing a composition for controllingunwanted microorganisms comprising mixing one or moreoxathiincarboxamides of formula (I) as claimed in claim 19 with one ormore extenders and/or surfactants.
 31. A halooxathiincarboxamide offormula (IV)

in which G¹ represents halogen, trifluoromethyl, difluoromethyl, orcyclopropyl, G² and G³ independently of one another represent hydrogenor methyl, n represents 0, 1 or 2, R¹, R², R³, and R⁴ independently ofone another represent hydrogen, fluorine, chlorine, methyl, isopropyl,or methylthio, R⁵ represents hydrogen, C₁-C₈-alkyl, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl;represents C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl,halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl having in eachcase 1 to 9 fluorine, chlorine, and/or bromine atoms; representsformyl-C₁-C₃-alkyl, (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl, or(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl; represents(C₁-C₃-haloalkyl)carbonyl-C₁-C₃-alkyl or(C₁-C₃-haloalkoxy)-carbonyl-C₁-C₃-alkyl having in each case 1 to 7fluorine, chlorine, and/or bromine atoms; represents(C₁-C₃-alkyl)carbonyl-C₁-C₃-haloalkyl or(C₁-C₃-alkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 6fluorine, chlorine, and/or bromine atoms; represents(C₁-C₃-haloalkyl)carbonyl-C₁-C₃-haloalkyl or(C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 13fluorine, chlorine, and/or bromine atoms; or represents —COR⁶, —CONR⁷R⁸,or —CH₂NR⁹R¹⁰, R⁶ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl; representsC₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, orC₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine,and/or bromine atoms; or represents —COR¹¹, R⁷ and R⁸ independently ofone another represent hydrogen, C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,or C₃-C₈-cycloalkyl; represent C₁-C₈-haloalkyl,halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl having in eachcase 1 to 9 fluorine, chlorine, and/or bromine atoms; or R⁷ and R⁸together with the nitrogen atom to which they are attached form asaturated heterocycle having 5 to 8 ring atoms, where the heterocycleoptionally contains 1 or 2 further nonadjacent heteroatoms selected fromthe group consisting of oxygen, sulphur, and NR¹² and is optionallymono- or polysubstituted by identical or different substituents selectedfrom the group consisting of halogen and C₁-C₄-alkyl, R⁹ and R¹⁰independently of one another represent hydrogen, C₁-C₈-alkyl, orC₃-C₈-cycloalkyl; or represent C₁-C₈-haloalkyl, C₃-C₈-halocycloalkylhaving in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; orR⁹ and R¹⁰ together with the nitrogen atom to which they are attachedform a saturated hetero-cycle having 5 to 8 ring atoms, where theheterocycle optionally contains 1 or 2 further nonadjacent heteroatomsselected from the group consisting of oxygen, sulphur, and NR¹² and isoptionally mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of halogen andC₁-C₄-alkyl, R¹¹ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl; representsC₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, orC₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine,and/or bromine atoms, R¹² represents hydrogen or C₁-C₆-alkyl, and X²represents bromine or iodine.
 32. An oxathiincarboxamideboronic acidderivative of formula (VI)

in which G¹ represents halogen, trifluoromethyl, difluoromethyl, orcyclopropyl, G² and G³ independently of one another represent hydrogenor methyl, n represents 0, 1 or 2, R¹, R², R³, and R⁴ independently ofone another represent hydrogen, fluorine, chlorine, methyl, isopropyl,or methylthio, R⁵ represents hydrogen, C₁-C₈-alkyl, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl;represents C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl,halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl having in eachcase 1 to 9 fluorine, chlorine, and/or bromine atoms; representsformyl-C₁-C₃-alkyl, (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl, or(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl; represents(C₁-C₃-haloalkyl)carbonyl-C₁-C₃-alkyl or(C₁-C₃-haloalkoxy)-carbonyl-C₁-C₃-alkyl having in each case 1 to 7fluorine, chlorine, and/or bromine atoms; represents(C₁-C₃-alkyl)carbonyl-C₁-C₃-haloalkyl or(C₁-C₃-alkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 6fluorine, chlorine, and/or bromine atoms; represents(C₁-C₃-haloalkyl)carbonyl-C₁-C₃-haloalkyl or(C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 13fluorine, chlorine, and/or bromine atoms; or represents —COR⁶, —CONR⁷R⁸,or —CH₂NR⁹R¹⁰, R⁶ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl; representsC₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, orC₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine,and/or bromine atoms; or represents —COR¹¹, R⁷ and R⁸ independently ofone another represent hydrogen, C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,or C₃-C₈-cycloalkyl; represent C₁-C₈-haloalkyl,halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl having in eachcase 1 to 9 fluorine, chlorine, and/or bromine atoms; or R⁷ and R⁸together with the nitrogen atom to which they are attached form asaturated heterocycle having 5 to 8 ring atoms, where the heterocycleoptionally contains 1 or 2 further nonadjacent heteroatoms selected fromthe group consisting of oxygen, sulphur, and NR¹² and is optionallymono- or polysubstituted by identical or different substituents selectedfrom the group consisting of halogen and C₁-C₄-alkyl, R⁹ and R¹⁰independently of one another represent hydrogen, C₁-C₈-alkyl, orC₃-C₈-cycloalkyl; or represent C₁-C₈-haloalkyl, C₃-C₈-halocycloalkylhaving in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; orR⁹ and R¹⁰ together with the nitrogen atom to which they are attachedform a saturated hetero-cycle having 5 to 8 ring atoms, where theheterocycle optionally contains 1 or 2 further nonadjacent heteroatomsselected from the group consisting of oxygen, sulphur, and NR¹² and isoptionally mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of halogen andC₁-C₄-alkyl, R¹¹ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl; representsC₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, orC₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine,and/or bromine atoms, R¹² represents hydrogen or C₁-C₆-alkyl, and A³ andA⁴ each represent hydrogen or together represent tetramethylethylene.33. A hydroxyalkyloxathiincarboxamide of formula (VIII)

in which G¹ represents halogen, trifluoromethyl, difluoromethyl, orcyclopropyl, G² and G³ independently of one another represent hydrogenor methyl, n represents 0, 1 or 2, R¹, R², R³, and R⁴ independently ofone another represent hydrogen, fluorine, chlorine, methyl, isopropyl,or methylthio, R⁵ represents hydrogen, C₁-C₈-alkyl, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl;represents C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl,halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl having in eachcase 1 to 9 fluorine, chlorine, and/or bromine atoms; representsformyl-C₁-C₃-alkyl, (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl, or(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl; represents(C₁-C₃-haloalkyl)carbonyl-C₁-C₃-alkyl or(C₁-C₃-haloalkoxy)-carbonyl-C₁-C₃-alkyl having in each case 1 to 7fluorine, chlorine, and/or bromine atoms; represents(C₁-C₃-alkyl)carbonyl-C₁-C₃-haloalkyl or(C₁-C₃-alkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 6fluorine, chlorine, and/or bromine atoms; represents(C₁-C₃-haloalkyl)carbonyl-C₁-C₃-haloalkyl or(C₁-C₃-haloalkoxy)carbonyl-C₁-C₃-haloalkyl having in each case 1 to 13fluorine, chlorine, and/or bromine atoms; or represents —COR⁶, —CONR⁷R⁸,or —CH₂NR⁹R¹⁰, R⁶ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl; representsC₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, orC₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine,and/or bromine atoms; or represents —COR¹¹, R⁷ and R⁸ independently ofone another represent hydrogen, C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,or C₃-C₈-cycloalkyl; represent C₁-C₈-haloalkyl,halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-halocycloalkyl having in eachcase 1 to 9 fluorine, chlorine, and/or bromine atoms; or R⁷ and R⁸together with the nitrogen atom to which they are attached form asaturated heterocycle having 5 to 8 ring atoms, where the heterocycleoptionally contains 1 or 2 further nonadjacent heteroatoms selected fromthe group consisting of oxygen, sulphur, and NR¹² and is optionallymono- or polysubstituted by identical or different substituents selectedfrom the group consisting of halogen and C₁-C₄-alkyl, R⁹ and R¹⁰independently of one another represent hydrogen, C₁-C₈-alkyl, orC₃-C₈-cycloalkyl; or represent C₁-C₈-haloalkyl, C₃-C₈-halocycloalkylhaving in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; orR⁹ and R¹⁰ together with the nitrogen atom to which they are attachedform a saturated hetero-cycle having 5 to 8 ring atoms, where theheterocycle optionally contains 1 or 2 further nonadjacent heteroatomsselected from the group consisting of oxygen, sulphur, and NR¹² and isoptionally mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of halogen andC₁-C₄-alkyl, R¹¹ represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₃-C₈-cycloalkyl; representsC₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, orC₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine,and/or bromine atoms, R¹² represents hydrogen or C₁-C₆-alkyl, and X⁵represents C₂-C₂₀-hydroxyalkyl that is optionally additionally mono- orpolysubstituted by identical or different substituents selected from thegroup consisting of halogen and C₃-C₆-cycloalkyl in which the cycloalkylmoiety is optionally substituted by halogen and/or C₁-C₄-alkyl.
 34. Anoxathiincarboxylic acid derivative of formula (II) selected from thegroup consisting of


35. An aniline derivative of formula (III) selected from the groupconsisting of